具有环氧化酶-2选择性抑制活性的多取代蒽醌的合成
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摘要
1-甲基-2-甲氧羰基-3, 6, 8-三羟基-7-甲氧基蒽醌是从唐菖蒲干球茎中分离到的具有环氧化酶-2选择性抑制活性的多取代蒽醌类化合物。本文试图合成该化合物,实现了其类似物的合成,同时发现了几个未见报道的反应。
1.通过Diels-Alder反应合成了关键中间体——3-甲基-5-羟基-1, 2, 4-苯三甲酸三甲酯,1-COOMe选择性水解产物与1, 2, 3-三甲氧基苯进行分子间Friedel-Crafts反应的产物再进行分子内Friedel-Crafts反应得到了目标产物的类似物1-甲基-2-甲氧羰基-3-羟基-6,7,8-三甲氧基蒽醌(路线1)。目标产物及其它类似物的合成正在进行中。
2.以乙酰乙酸甲酯和巴豆醛为原料,经过Michael加成、分子内的Aldol反应、芳香化、选择性甲酰化和还原反应,得到关键中间体2-甲基-3-羟甲基-6-甲氧基苯甲酸甲酯及其衍生物。通过该化合物与3,4,5-三甲氧基苯甲酸甲酯进行Friedel-Crafts烷基化反应得到了多取代的二苯基甲烷衍生物,拟进一步关环合成目标化合物(路线2)。
3.发现邻甲氧基苯甲酸甲酯中酯甲基可以被正丁基锂和仲丁基锂中烷基交换生成相应的酯,反应的机理不明确。当使用叔丁基锂时,得到的是邻甲氧基苯基叔丁酮,这个方法可以用来合成芳基叔丁酮类化合物。
4.以2-苄氧基-6-甲基苯甲酸甲酯为原料进行氯甲基化反应时,以苯和二氯乙烷作溶剂,发生了苄基的迁移和芳环的偶联,分别得到2,2'-二甲基-3,3'-二甲氧羰基-4,4'-二羟基联苯和2,2'-二甲基-3,3'-二甲氧羰基-4,4'-二羟基-5,5'-二苄基联苯。这是对称联苯合成的新方法。
5.水杨酸羟基邻对位的选择性甲酰化可以分别通过水杨酸和水杨酸甲酯用HMTA/CF3COOH来实现。
6.Lewis酸催化3,4,5-三甲氧基苄醇环化成1, 2, 3, 6, 7, 8, 11, 12, 13-nonamethoxyl-10,15-dihydro-5H-trbibenzo [a, d, g] cyclononene (NDTC),产率(54%)高于已有方法(12%)。
Methyl 3,6,8-trihydroxy-7-methoxy-1-methylanthraquinone-2-carboxylate is a new COX-2 selective inhibitor isolated from Gladiolus gandavensis. Two strategies were investigated to synthesis this compound, in which some important reactions were discovered.
1. The key intermediate 5-hydroxy-3-methylbenzene-1,2,4-tricarboxylic acid 2,4-dimethyl ester was prepared via Diels-Alder reaction followed by selective hydrolysis of 1-COOMe. This compound was coupled with 1,2,3-trimethoxybenzene and the product undergo intramolecular Friedel-Crafts reaction to give methyl 3-hydroxy-5,6,7-trimethoxy-1-methylanthraquinone-2-carboxylate (1st route). The target compound and other analogues are being prepared with the same procedure.
2. The key intermediates methyl 3-hydroxymethyl-6-methoxy-2-methylbenzoate and its derivatives were prepared starting from crotonaldehyde and methyl acetoacetate via Michael addition, intramolecular aldol reaction, aromatization, formylation and reduction. The intermediates were coupled respectively with derivatives of gallic acid to give polysubstituted diphenylmethane. However, attempts to cyclize these compounds to the target compounds and analogues were not successful (2nd route).
3. In the process for ortho-lithiation of methyl 2-methoxybenzoate, the substrate converted respectively to n-butyl 2-methoxybenzoate and sec-butyl 2-methoxybenzoate when n-BuLi and sec-BuLi were used. However, tert-BuLi reacted with methyl 2-methoxybenzoate afford 2-methoxyphenyl tert-butyl ketone, which could be used to synthesize aryl tert-butyl ketones.
4. The transformtion of methyl 2-benzoxy-6-methylbenzoate to dimethyl 4,4'-dihydroxy-2,2'-dimethylbiphenyl-3,3'-dicarboxylate in benzene, and dimethyl 5,5'-dibenzyl-4,4'-dihydroxy-2,2'-dimethylbiphenyl-3,3'-dicarboxylate in 1,2-dichloroethane in the presence of ZnCl2 provides a new method for the synthesis of symmetric biphenyl.
5. The formylation of salicylic acid at C-5 and methyl 2-hydroxybenzoate at C-3
1.通过Diels-Alder反应合成了关键中间体——3-甲基-5-羟基-1, 2, 4-苯三甲酸三甲酯,1-COOMe选择性水解产物与1, 2, 3-三甲氧基苯进行分子间Friedel-Crafts反应的产物再进行分子内Friedel-Crafts反应得到了目标产物的类似物1-甲基-2-甲氧羰基-3-羟基-6,7,8-三甲氧基蒽醌(路线1)。目标产物及其它类似物的合成正在进行中。
2.以乙酰乙酸甲酯和巴豆醛为原料,经过Michael加成、分子内的Aldol反应、芳香化、选择性甲酰化和还原反应,得到关键中间体2-甲基-3-羟甲基-6-甲氧基苯甲酸甲酯及其衍生物。通过该化合物与3,4,5-三甲氧基苯甲酸甲酯进行Friedel-Crafts烷基化反应得到了多取代的二苯基甲烷衍生物,拟进一步关环合成目标化合物(路线2)。
3.发现邻甲氧基苯甲酸甲酯中酯甲基可以被正丁基锂和仲丁基锂中烷基交换生成相应的酯,反应的机理不明确。当使用叔丁基锂时,得到的是邻甲氧基苯基叔丁酮,这个方法可以用来合成芳基叔丁酮类化合物。
4.以2-苄氧基-6-甲基苯甲酸甲酯为原料进行氯甲基化反应时,以苯和二氯乙烷作溶剂,发生了苄基的迁移和芳环的偶联,分别得到2,2'-二甲基-3,3'-二甲氧羰基-4,4'-二羟基联苯和2,2'-二甲基-3,3'-二甲氧羰基-4,4'-二羟基-5,5'-二苄基联苯。这是对称联苯合成的新方法。
5.水杨酸羟基邻对位的选择性甲酰化可以分别通过水杨酸和水杨酸甲酯用HMTA/CF3COOH来实现。
6.Lewis酸催化3,4,5-三甲氧基苄醇环化成1, 2, 3, 6, 7, 8, 11, 12, 13-nonamethoxyl-10,15-dihydro-5H-trbibenzo [a, d, g] cyclononene (NDTC),产率(54%)高于已有方法(12%)。
Methyl 3,6,8-trihydroxy-7-methoxy-1-methylanthraquinone-2-carboxylate is a new COX-2 selective inhibitor isolated from Gladiolus gandavensis. Two strategies were investigated to synthesis this compound, in which some important reactions were discovered.
1. The key intermediate 5-hydroxy-3-methylbenzene-1,2,4-tricarboxylic acid 2,4-dimethyl ester was prepared via Diels-Alder reaction followed by selective hydrolysis of 1-COOMe. This compound was coupled with 1,2,3-trimethoxybenzene and the product undergo intramolecular Friedel-Crafts reaction to give methyl 3-hydroxy-5,6,7-trimethoxy-1-methylanthraquinone-2-carboxylate (1st route). The target compound and other analogues are being prepared with the same procedure.
2. The key intermediates methyl 3-hydroxymethyl-6-methoxy-2-methylbenzoate and its derivatives were prepared starting from crotonaldehyde and methyl acetoacetate via Michael addition, intramolecular aldol reaction, aromatization, formylation and reduction. The intermediates were coupled respectively with derivatives of gallic acid to give polysubstituted diphenylmethane. However, attempts to cyclize these compounds to the target compounds and analogues were not successful (2nd route).
3. In the process for ortho-lithiation of methyl 2-methoxybenzoate, the substrate converted respectively to n-butyl 2-methoxybenzoate and sec-butyl 2-methoxybenzoate when n-BuLi and sec-BuLi were used. However, tert-BuLi reacted with methyl 2-methoxybenzoate afford 2-methoxyphenyl tert-butyl ketone, which could be used to synthesize aryl tert-butyl ketones.
4. The transformtion of methyl 2-benzoxy-6-methylbenzoate to dimethyl 4,4'-dihydroxy-2,2'-dimethylbiphenyl-3,3'-dicarboxylate in benzene, and dimethyl 5,5'-dibenzyl-4,4'-dihydroxy-2,2'-dimethylbiphenyl-3,3'-dicarboxylate in 1,2-dichloroethane in the presence of ZnCl2 provides a new method for the synthesis of symmetric biphenyl.
5. The formylation of salicylic acid at C-5 and methyl 2-hydroxybenzoate at C-3
引文
1. M. Kitajima, U. Fischer, M. Nakamur, M. O. Masahiro, Anthraquinones from Ophiorrhiza Pumilatissue and cell cultures, Phytochemistry, 1998, 48 (1), 107-111.
2. P. N. Solis, A. G. Ravelo, A. G. Gonzalez, M. P. Gupta, J. D. Phillipson, Boiacitve anthraquinone glycosides from Picramnia Antidesma SSP. Fessonia, Phytochemistry, 1995, 38 (2), 477-480.
3. J. Kinjo, T. Ikeda, K. Watanbe, T. Nohara, An anthraquinone glycoside from Cassia Angustifolia leaves, Phytochemistry, 1994, 37 (6), 1685-1685.
4. A. A. El-Gamal, K. Takeya, H. Itokawa, A. F. Halm, M. M. Amer, H. A. Saad, S. A. Awad, Anthraquinone from Galium Sinaicum, Phytochemistry, 1995, 40 (1), 245-251.
5. C. N. Lin, B. L. Wei, Anthroquinone and naphthalene glycosides from Rhamus Nakaharai, Phytochemistry, 1993, 33 (4), 905-908.
6. I. Kubo, Y. Murai, I. Soediro, S. Soetaino, S. Sastrodihardjo, Cytotoxic anthraquinone from Rheum Pulmatum, Phytochemistry, 1992, 31 (3), 1063-1065.
7. M. Kazmi, A. Malik, S. Hameed, N. Akhtar, S. N. Ali, An anthraquinone derivative from Cassia Italica, Phytochemistry, 1994, 36 (3), 761-763.
8. P. A. Cohen, G. H. N. Towers, The anthroquinones of Heterodermia Obscurata, Phytochemistry, 1995, 40 (3), 911-915.
9. D. V. Banthorpe, J. J. White, Novel anthraquinones from undifferentiated cell cultures of Galium Verum, Phytochemistry, 1995, 38 (1), 107-111.
10. Z. Zhou, S. H. Jiang, D. Y. Zhu, L. Z Lin, G. A. Cordell, Anthraquinones from Knoxia Valerianoides, Phytochemistry, 1994, 36 (3), 765-768.
11. E. Dagne, A. Yenesew, S. Asmellash, S. Demissew, S. Mav, Anthraquinones, pre-anthraquinones and isoeleutherol in the roots of Aloe species, Phytochemistry, 1994, 35 (2), 401-406.
12. L. F. Van Staden, S. E. Drewes, Knipholone from bulbine latifolia and bulbinefrutescens, Phytochemistry, 1994, 35 (3), 685-686.
13. J. Koyama, J. Ogura, K. Tagahara, Anthraquinones of Galium Spurium, Phytochemistry, 1993, 33 (6), 1540-1542.
14. B. L. Wei, C. N. Lin, S. J. Won, Nakahalene and cytotoxic priciples of Formosan Rhamnus species, J. Nat. Prod., 1992, 55 (7), 967-969.
15. P. A. Cohen, G. H. N. Towers, Anthrawuinones and phenanthroper; enequinones from Nephroma Laevigtum, J. Nat. Prod., 1995, 58 (4), 520-526.
16. J. Koyama, T. Ogura, K. Tagahara, T. Konoshima, M. Kozuka, Two naphthoquinones from Rubia Cordifola, Phytochemistry, 1992, 31 (8), 2907-2908.
17. X. Z. Lu, W. H. Xu, H. Naoki, Anthraquinones from Salvia Przewalskii, Phytochemistry, 1992, 31 (2), 708-709.
18. B. Barba, J. G. Dlaz, W. Herz, Anthraquinones and other constituents of two Senna species, Phytochemistry, 1992, 31 (12), 4734-4735.
19. T. K. Yadav, S. B. Kalidar, Alquinone: An anthraquinone from Cassia alata, Planta Med., 1994, 60, 601-603.
20. B. Jaki, J. Heilman, O. Sticher, New antibacterical metabolites from the cyanobacterium Nostoc commune (EAWAG 122b), J. Nat. Prod., 2000, 63 (9), 1283-1285.
21. M. Morimoto, K. Tanimoto, A. Sakatani, K. Komai, Antifeedant activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F., Phytochemistry, 2002, 60, 163-166.
22. B. L. Wei, C. M. Lu, L. T. Tsao, J. P. Wang, C. N. Lin, In vitro anti-inflammatory effects of quercetin 3-O-methyl ether and other constituents from Rhamnus species, Planta Med., 2001, 67, 745-747.
23. J. Koyama, T. Okatani, K. Tagahara, I. Kouno, H. Irie, Anthraquinones of Damnacanthus Indicus, Phytochemistry, 1992, 31 (2), 709-710.
24. G. Bringmann, D. Menche, M. Bezabih, B. M. Abegaz, R. Kaminsky, Antiplasmodial activity of Knipholone and related natural phenylanthraquinones,Planta Med., 1999, 65, 757-758.
25. M. A. Qhotasokane-Lusunzi, P. Karuso, Secondary metabolitics from basotho medicinal plants.Ⅰ. Bulbine narcissifola, J. Nat. Prod., 2001, 64, 1368-1372.
26. G. Brauers, R. A. Edrada, R. Ebel, P. Proksch, V. Wray, A. Berg, U. Gr?fe, C. Sch?chtele, F. Totzke, Anthraquinones and betaenone derivatives from the sponge-associated fugus Microphaeropsis species: novel inhibitors of protein kinases, J. Nat. Prod., 2000, 63 (6), 739-745.
27. 向兰,郑俊华,果德安,寇晋萍,范国强,段豫萍,秦晨,窄叶大黄醌类化学成分研究,中草药,2001,32(5),395-396。
28. A. R. Bilia, A. W. Yusuf, A. Braca, A. Keita, I. Morelli, New prenylated anthraquinones and xanthones from Vismia guineesis, J. Nat. Prod., 2000, 63, 16-21.
29. 邱峰,徐金钟,段文娟,曲戈霞,王乃利,姚新生,红葱中的新化学成分,高等学校化学学报,2005,26(11),2057-2060。
30. D. Carins, E. Michalitsi, T. C. Jenkins, S. P. Mackay, Molecular modeling and cytotoxicity of substituted anthraquinones as inhibitors human telomerase, Bioorganic & medicinal chemistry, 2002, 803-807.
31. J. Koyama, I. Morita, K. Tagakazu, M. Ogata, T. Mukainaka, H. Tokuda, H. Nishino, Inhibtory effects of anthraquinones and bianthraquinones on Epstein-Barr virus activation, Cancer Lett., 2001, 170, 15-18.
32. G. Z. Jin, Y. J. You, Y. Kim, N. H. Nam, B. Z. Ahn, Esters of chlorambucil with 2-substituted 1,4-dihydroxy-9,10-anthraquinones as multifunctional anticancer agents, Eur. J. Med. Chem.,2001, 36, 361-366.
33. 王定勇,唐菖蒲和飞蛾藤的化学成分研究,中国科学院博士学位论文,2003。
34. M. Chrysayi-Tokousbalides, M. A. Kastanias, Cynodontin: A fungal metabolite with antifungal properties, J. Agric. Food Chem., 2003, 51 (17), 4920-4923.
35. G. Meazza, F. E. Dayan, D. E. Wedge, Activity of quinones on Colletotrichum species, J. Agric. Food Chem., 2003, 51 (13), 3824-3828.
36. B. S. Park, J. R. Kim, S. E. Lee, K. S. Kim, G. R. Takeoka, Y. J. Ahn, J. H. Kim,
Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria, J. Agric. Food Chem., 2005, 53 (4), 1152-1157.
37. K. Mitura, H. Kikuzaki, N. Nakatani, Antioxidant activity of chemical components from Sage (Salvia officinalis L.) and Thyme (Thymus vulgaris L.) measured by the oil stability index method, J. Agric. Food Chem., 2002, 50 (7), 1845-1851.
38. N. V. S. Ramakrishna, K. H. S. Swamy, E. K. S. V. Kumar, M. M. S. Kushwaha, S. Kota, M. Raman, S. D Tare, S. K. Deshmukh, D. Schummer, M. Kurz, H. Kogler, Patents PTC/EP99/04127 and WO 99-67408 A1.
39. L. Vertesy, M. Kurz, E. F. Paulus, D. Schummer, P. Hammann, J. Antibiot., 2001, 54, 354-363。
40. B. L. Wei, S. H. Wu, M. I. Chung, S. J. Won, C. N. Lin, Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives, Eur. J. Med. Chem., 2000, 35, 1089-1098.
41. W. Werner, U. Gr?fe, W. Ihn, D. Tresselt, S. Winter, E. Paulus, Synthesis of Tolypocladin and Isotolypocladin, Tetrahedron, 1997, 53 (1), 109-118.
42. K. S. Kim, M. W. Spatz, F. Johnson, Anthracyclines and related substancesⅠ. A new Friedel-Crafts alkylation reaction using 3-Bromophthalides. Efficient synthesis of islandicin, Tetrahedron Lett., 1979, 20 (4), 331-334.
43. M. L. Patil, H. B. Borate, D. E. Ponde, V. H. Deshpande, Total synthesis of (±)-brasiliquinone B, Tetrahedron, 2002, 58, 6615-6620.
44. Mahesh L. Patil, Hanumant B. Borate, Datta E. Ponde, Baburao M. Bhawal, Visum H. Deshpande, First total synthesis of (±)-brasiliquinone B, Tetrahedron Lett., 1999, 40, 4437-4438.
45. D. L. Boger, J. Hong, M. Hikota, M. Ishida, Total synthesis of Phomazarin, J. Am. Chem. Soc., 1999, 121, 2471-2477.
46. B. Caron, P. Brassard, An integrated approach to the synthesis of contiguously substituted xanthopurpurins, pachybasins and purpurrins, Tetrahedron, 1993, 49(4), 771-784.
47. M. Gill, P. M. Morgan, J. M. White, J. Yu, Pigments of fungi. XLⅦ cardinalic acid, a new anthraquinone carboxylic acid from the New Zealand Dermocybe cardinalis and synthesis and X-ray crystal structure of methyl 1,7,8-tri-o-methylcardinalate, Aust. J. chem., 1998, 51, 213-218.
48. K. Krohn, J. Micheel, M. Zukowski, Total synthesis of angucyclines. Part 15: a short synthesis of (±)-6-deoxybrasiliquinone B, Tetrahedron, 2000, 56, 4753-4758.
49. D. W. Cameron, C. Corn, G. I. Feutrill, Chemistry of the coccoidea Ⅱsynthesis of ceroalblinic acid, Aust. J. Chem., 1981, 34, 1945.
50. J. M. Pérez, P. López-Alvarado, C. Avenda?o, J. C. Menéndez, Hetero Diels-Alder reactions of 1-acetylamino- and 1-dimethylamino-1-azadienes with benzoquinones, Tetrahedron, 2000, 56, 1561-1567.
51. K. Kobayashi, M. Uchida, S. Watanabe, A. Takanohashi, M. Tanmatsu, O. Morikawa, H. Konishi, Synthesis of 1-amino- and 1-hydroxy-9, 10-anthraquinone derivative based on reaction sequences between 2-acetyl-1,4-naphthraquinone and enamines, Tetrhedron Lett., 2000, 41, 2381-2384.
52. G. A. Kraus, H. Cho, S. Crowley, B. Roth, H. Sugimoto, S. Prugh; Phthalide annulation: the synthesis of kalafungin, pachybasin and chrysophanol. J. Org. Chem., 1983, 48 (20), 3439-3444.
53. M. Braun, A regioselective synthesis of daunomycinone and related anthracyclinones, Tetrahedron, 1984, 40 (22), 4585-4591.
54. S. O. de Silva, M. Watanabe, V. Snieckus, General route to anthraquinone natural products via directed metalation of N,N-diethylbenzamides, J. Org. Chem., 1979, 44 (26), 4802-4808.
55. K. C. Nicolaou, J. L.Gross, M. A. Kerr, R. H. Lemus, K.Ikeda, K. Ohe, Synthesis of the anthraquinone framework of Dynemicin A, Angew. Chem. Int. Ed. Engl., 1994, 33 (7), 781-783.
56. H. Zhao, E. Biehl, Preparation of naturally occurring anthraquinone using arynereaction, J. Nat. Prod., 1995, 58 (12), 1970-1974.
57. F. Kaiser, L. Schwink, J. Velder, H. G. Schmalz, Studies towards the total synthesis of mumubaistatin: synthesis of highly substituted benzophenone and anthraquinone building block, Tetrahedron, 2003, 59, 3201-3217.
58. C. A. Townsend, S. G. Davis, S. B. Christensen, J. C. Link, C. P. Lewis, Methoxymethyl-directed aryl metalation. A total synthesis of (±)-averufin, J. Am. Chem. Soc., 1981, 103, 6885-6888.
59. M. Watanabe, E. Shinoda, Y. Shimizu, S. Furukawa, Synthesis of bostrycoidin via lithiation of tertiary nicotinamide, Tetrahedron, 1987, 43 (22), 5281-5286.
60. D. L. Boger, J. Hong, M. Hikota, M. Ishida, Total synthesis of phomazarin, J. Am. Chem. Soc., 1999, 121, 2471-2477.
61. B. J. Whitlock, H. W. Whitlock, Regiospecific synthesis of islandicin methyl ether, J. Org. Chem., 1980, 45 (1), 12-15.
62. N. R. Ayyangar, J. Sci. Industr. Res., 1961, 20B, 493.
63. A. Kalogerakis, U. Groth, Synthesis of the benzo[а]anthraquinone core of angucylinone antibiotics, Org. Lett., 2003, 5 (6), 843-844.
64. F. E. McDonald, H. Y. H. Zhu, C. R. Holmquist,Rhodium-catalyzed alkyne cyclotrimerization strategies for C-aryl glycoside synthesis, J. Am. Chem. Soc., 1995; 117 (24); 6605-6606.
1. J. R. Vane, Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs, Nature (New Biol.), 1971, 231, 232-235.
2. 王庆利,盛春元,赵桂宏,新型非甾体抗炎药 COX-2 选择性抑制剂的研究及应用前景,中国药房,2001, 12 (5), 304-305。
3. J. L. Masferrer, K. Seibert, B. S. Zwefei, The induction and suppression of prostaglandin H2 synthase (cyclooxygenase) in human monocytes, J. Biol. Chem., 1990, 265, 16737-16741.
4. W. Xie, J. G. Chipman, D. L. Robert, Expreesion of a mitogen-resposive gene ecoding prostaglandin synthase is regulated by mRNA splicing, Proc. Natl. Acad. Sci. USA, 1991, 88, 2692-2699.
5. I. Siegle,T. Klein,J. T. Packman, Expression of cyclooxygenase-1 and cyclooxygenase-2 in human synovial tissue : Diferential elevation of cyclooxygenase-2 in inflammatoryjoint diseases, Arthritis Rheum, 1998,4l, l22-.
6. J. P. Famay, In vitro and in vivo pharmacological evidence of selective cyclooxygenase-2 inhibition by nime sulide:an overview, Influmm. Res,1997, 46, 437.
7. J. A. Mitchell, P. Alarasereenot, J. R. Vane, Pharmacological and biochemical demonstration of the role cyclooxygenase-2 in inflammation and pain, Proc. Natl. Acad. Sci. USA, 1993, 90, 11693-11697.
8. G. A. Fitzgerald, Coxibs and cardiovascular disease, N. Engl. J. Med., 2004, 351(17), 1709 - 1711.
9. K. Shinmura, X. L. Tang, Y. Wang, Cyclooxygenase-2 mediates the cardioprotective effects of the late phase of ischemic preconditioning in conscious rabbits, Proc. Natl. Acad. Sci. USA, 2000, 97 (18), 10197 - 10202.
10. S. D. Solomon, J. J. MeMurray, M. A. Pfeffer, Cardiovascular risk associated with celecoxib in a clinical trial for colorectal adenoma prevention, N. Engl. J. Med., 2005, 352, 1071-1080.
11. D. Mukherjee, E. J. Topol, COX-2: where are we in 2003? Cardiovascular risk and COX-2 inhibitors, Arthritis. Res. Ther., 2003, 5 (1), 8 - 11.
12. D. Y. Wang, Q. Ye, B. G. Li, G. L. Zhang, A new anthraquinone from Gladiolus gandavensis, Nat. Prod. Res., 2003, 17 (5), 365-368.
13. D. Y. Wang, Q. Ye, B. G. Li, G. L. Zhang, New anthraquinones from Gladiolus gandavensis, J. Asian Prod. Res., 2003, 5 (4), 297-301.
14. B. Chen, D. Y. Wang, Q. Ye, B. G. Li, G. L. Zhang, Anthraquinones from Gladiolus gandavensis, J. Asian Prod. Res., 2003, 5 (4), 297-301.
15. T. Danishesky, T. Kitahara, A useful diene for Diels-Alder reaction, J. Am. Chem. Soc., 1974, 96 (25), 7807-7808.
16. J. W. Patterson, The Alder-Rickert reaction in a synthesis of m-chlorophenols and 4-chloromycophenolic acid, J. Org. Chem., 1995, 60 (3), 560-563.
17. A. Barbero, F. J. Pulido, Isoxazoles as latent siloxybutadienes: an easy entry to polyfunctionalized benzene systems via Diels-Alder reaction with acetylenes, Synthesis, 2004, 3, 401-404.
18. C. Pulgarin, J. Gunzinger, R. Tabacchi, Synthèse de l’ériodermine, Helv. Chim. Acta., 1985, 68, 945-948.
19. A. A. Birkbeck, M. V. Sargent, J. A. Elix, The atructure of the lichen depsidones fulgidin and isofulgidin, Aust. J. Chem., 1990, 43, 419-425.
20. J. A. Elix, K. L. Gaul, H. Jiang, The structure and synthesis of some minor xanthones from the lichen rinodina thiomela, Aust. J. Chem.,1993, 46, 95-110.
21. M. L. Patil, H. B. Borate, D. E. Ponde, V. H. Deshpande, Total synthesis of (±)-brasiliquinone B, Tetrahedron, 2002, 58, 6615-6620.
22. J. P. Hwang, G. K. S. Prakash, G. A. Olah, Trifuoromethanesulfonic acid catalyzed novel Friedel-Crafts acylation of aromatics with methyl benzoate, Tetrahedron, 2000, 56, 7199-7203.
23. A. G. Schultz, S. A. Hardinger, Photochemical and acid-catalyzed dienone-phenol rearrangement. The effect of substituents on the regioselectivity of 1,4-sigmatrtropic rearrangements of the type A intermediate, J. Org. Chem., 1991, 56, 1105-1111.
24. V. Snieckus, Directed ortho metalation. Tertary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics, Chem. Rev., 1990, 90 (6), 879 – 933.
25. J. J. Court, D. J. Hlasta, Ortho versus adjacent-benzylic directed lithiations of substituted N,N-diethylbenzamides, Tetrahedron Lett., 1996, 37 (9), 1335-1338.
26. J. Clayden, J. H. Pink, N. Westlund, F. X. Wilson, Controlling the regioselectivity of lithiation using kinetic isotope effects: deuterium as protecting group forcarbon, Tetrahedton Lett., 1998, 39, 8377-8380.
27. D. Tilly, S. S. Samanta, F. Faigl, J. Mortier, Combined directed ortho metalation–intrqmolecular Friedel-Crafts connections. Regiospecific route to 1-substituted fluoren-9-ones, Tetrahedron Lett., 2002, 43, 8347-8350.
28. F. Gohier, J. Mortier, ortho-Metalation of unprotected 3-bromo and 3-chlorobenzoic acids with hindered lithium dialkylamides, J. Org. Chem., 2003, 68 (5), 2030-2033.
29. J. Kristensen, M. Lysén, P. Vedso, M. Begtrup, Synthesis of ortho substituted arylboronic ester by in situ trapping of unstable lithio intermediates, Org. Lett., 2001, 3 (10), 1435-1437.
30. W. A. Carroll, X. L. Zhang, Competitve ortho metalation effects: the kinetic and thermodynamic lithiation of 3- (tert-butoxycarbonyl)amino-4-carbomethoxythiophene, Tetrahedron Lett., 1997, 38(15), 2637-2640.
31. J. G.. Allen, S. J. Danishefsky, The total synthesis of (±)-rishirilide, J. Am. Chem. Soc., 2001, 123 (2), 351-352.
32. S. Dey, D. Mal, Total synthesis of BE-23254, a chlorinated angucycline antibiotic, Tetrahedron Lett., 2005, 46, 5483-5486.
33. L. Cleaver, J. A. Croft, E. Ritchie, W. C. Taylor, Chemical studies of the protaceae. Ⅸ. Synthesis of 5-alkylresorcinols from aliphatic precursors, Aust. J. Chem., 1976, 29, 1989-1995.
34. C. Pulgarin, R. Tabacchi, Synthèse de l’acide décarboxythamnolique, Helv. Chim.Acta., 1988, 71, 876-880.
35. C. Pulgarin, J. Gunzinger, R. Tabacchi, Synthèse des pseudocyphellarins A et B, deux depsides du lichen pseudocyphellaria endochrysea, Helv. Chim. Acta., 1985, 68, 1948-1951.
36. J. A. Elix, R. Naidu, G. Thor, Cyclofraphin, a new depdidone from the lichen catarraphia dictyolaca, Aust. J. Chem., 1995, 48, 635-649.
37. W. E. Wymann, R. Davis, J. W. Pattterson, J. R. Pfister, Selective alkylations of certain phenolic and enolic functions with lithium carbonate halide, Syn. Commun., 1988, 18 (12), 1379-1384.
38. A. J. Pearson, P. R. Brun, Studies on the synthesis of aryl ethers using areno-manganese chemistry, J. Org. Chem., 1991, 56 (25), 7092-7097.
39. C. F. Carvalho, A. V. Russo, M. V. Sargent, Boron trichloride as a selective demethylation agent for hindered ethers: a synthesis of the phytoalexins A and B pyrufran, a synthesis of tripopmehtylleprolomin and its demethylation, Aust. J. Chem., 1985, 777-792.
40. 景崤壁,任新锋,彭坤,武同兴,潘鑫复,选择性去甲醚化反应——3,5-二甲氧基 4-羟基苯甲酸甲酯的新合成方法,兰州大学学报(自然科学版),2001,37(3),78-79。
41. P. Lesot, D. Merlet, M. Sarfati, J. Courtieu, H. Zimmermann, Z. Luz, Enatiomeric and enantiotopic analysis of cone-shaped compounds with C3 and C3v symmetry using NMR spectroscopy in chiral anisotropic solvents, J. Am. Chem. Soc., 2002, 124 (34), 10071-10082.
42. M. Salmón, N. Zavala, M .Martínez, R. Cruz, Cyclic and linear oligomerization reaction of 3,4,5-trimethoxybenzyl alcohol with a Bentonite-clay, Tetrahedron Lett., 1994, 35 (32), 5797-5800.
43. G. Keum, H. J. Lim, S. B. Kang, Y. Kim, B. Y. Chung, Indium catalyzed Friedel-Crafts benzylation of aromatic compounds with benzyl halides, Bull. Korean Chem. Soc., 2000, 21 (8), 809-812.
44. G. A. Olah, J. A. Olah, T. Ohyama, Friedel-Crafts alkylation of anisole and its comparison with toluene. Predominant ortho-para substitution under kinetic conditions and the effect of thermodynamic isomerizations, J. Am. Chem. Soc., 1984, 106 (18), 5284-5290.
45. T. Yamato, M. Fukumoto, N. Sakaue, T. Furusawa, M. Tashiro, A new route for the synthesis of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene using Friedel-Crafts intramolecular cyclobenzylation, Synthesis, 1991, 9, 699-700.
46. S. Urgaonkar, H. S. La Pierre, I. Meir, H. Lund, D. RayChaudhuri, J. T. Shaw, Synthesis of antimicrobial natural products targeting FtsZ: (±)-dichamanetin and (±)-2’’’-hydroxy-5’’-benzylisouvarinol-B, Org. Lett. 2005, 7 (25), 5609-5612.
47. J. A. Ruell, E. De Clercq, C. Pannecouque, M. Witvrouw, T. L. Stup, J. A. Turpin, R. W. Buckheit, M. Cushman, Synthesis of anti-HIV activity of cosalane analogues with substituted benzoic acid rings attached to the pharmacophore through methylene and amide linkers, J. Org. Chem., 1999, 64 (16), 5858-5866.
48. T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa, Scandim (Ⅲ) triflate catalyzed Friedel-Crafts alkylation with benzyl and allyl alcohols, Synlett, 1996,557-559.
49. A. Ishii, O. Kotera, T. Saeki, K. Mikami, Trimethylsilyl bis(trifluoromethanesulfonyl)amide as a effective catalyst for Friedlel-Crafts alkylation reaction, Synlett, 1997, 6, 1145-1146.
50. T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa, Scandium(III) triflate-catalyzed Friedel-Crafts alkylation reactions, J. Org. Chem., 1997, 62 (20), 6997-7005.
51. T. Miyai, Y. Onishi, A. Baba, Novel reductive Friedel-Crafts alkylation of aromatics catalyzed by indium compounds: chemoselective utilization of carbonyl moieties as alkylating reagents, Tetrahedron, 1999, 55, 1017-1026.
52. T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa, Scandium(III) trifluoromethanesulfonate-catalysed reductive Friedel–Crafts benzylation of aromatic compounds using arenecarbaldehydes and propane-1,3-diol, Chem. Commun., 1996, 20, 2345-2346.
53. S. Fukuzawa, T. Tsuchimoto, K. Tobita, T. Hiyama, Superacid-catalyzed reductive Friedel-Crafts reaction of arenas using arenecarbaldehyde acetals, J. Org. Chem., 1997, 62, 151-156.
54. W. L. F.Armarego, D. D. Perrin,. Purification of Laboratory Chemicals. London, 1997, 4th ED.
1. Robinson, G.M. A Reaction of Homopiperonyl and of Homoveratryl Alcohols, J. Chem. Soc. 1915, 107, 267-276.
2. (a) A. S. Lindsey, The structure of cyclotriveratrylene (10,15-dihydro-2,3,7,8,12,13-hexamethoxy-5H-tribenzo[a,d,g]cyclononene) and related compounds, J. Chem. Soc., 1965, 1685-1691. (b) A. S. Lindsey, Cyclotroveratrylene and related compounds, Chem. Ind. (Lond), 1963, 823-824.
3. H. Erdtman, F. Haglid, R. Ryhage, Macrocyclic condensation products of veratrole and resorcinol, Acta. Chem. Scand., 1964, 18, 1249-1254.
4. A. Goldup, A. B. Morrison, G. W. Smith, The structure of cycloveratril, J. Chem. Soc., 1965, 3864-3866.
5. J. A. Hyatt, E. N. Duesler, D. Y. Curtin, I. C.Paul, Stoichiometric Inclusion compounds of cyclotriveratrylene and cyclotricatechylene with small neutral molecules. X-ray crystal structure of cyclotricatechylene di-2-propanolate. J. Org. Chem., 1980. 45 (25), 5074-5079.
6. (a) A. Collet, G. Gottarelli, Circular dichroism spectrum of C3-cyclotriguaiacylene after ionization of the phenolic groups. experimental approach to the magic angle region in C3-cyclotriveratrylene derivative, J. Am. Chem. Soc., 1982, 104 (25), 7383-7384; (b) A. Collet, G.. Gottarelli, The circular dichroism and absolute configuration of C3-chiral derivatives of cyclotriveratrylene, J. Am. Chem. Soc., 1981, 103 (1), 204-205.
7. (a) R. Ahmad, A. Franken, J. D. Kennedy, M. J.Hardie, Group 1 coordination chains and hexagonal networks of host cyclotriveratrylene with halogenated monocarbaborane anions, Chem. Eur. J., 2004, 10, 2190-219; (b) A. Arduini, F. Calzavacca, D. Demuru, A. Pochini, A. Secchi, Synthesis of cavity extended cyclotriveratrylenes, J. Org. Chem., 2004, 69 (4), 1386-1388; (c) T. Brotin, J. P. Dutasta, Xe@cryptophane complexes with C2 symmetry: synthesis and investigations by 129Xe NMR of the consequences of the size of the host cavity for xenon encapsulation, Eur. J. Org. Chem., 2003, 973-984; (d) D. S. Bohle, D. J. Stasko, Salicylaldiminato derivatives of cyclotriveratrylene: Flexible strategy for new rim-mMetalated CTV complexes, Inorg. Chem., 2000, 39, 5768-5770; (e) J. F. Nierengarten, L. Oswald, J. F. Eckert, J. F. Nicoud, N. Armaroli, Complexation of fullerenes with dendritic cyclotriveratrylene derivatives, Tetrahedron Lett., 1999, 40, 5681-5684; (f) M. J. Hardie, P. D.Godfrey, C. L. Raston, Self-assembly of grid and helical hydrogen-bonded arrays incorporating bowl-shaped receptor sites that bind globular molecules, Chem. Eur. J., 1999, 5 (6), 1828-1833; (g) K. T. Holman, M. M. Halihan, S. S. Jurisson, J. L. Atwood, R. S. Burkhalter, A. R. Mitchell, J. W. Steed, Inclusion of neutral and anionic guests within the cavity of π-metalated cyclotriveratrylenes, J. Am. Chem. Soc., 1996, 118 (40), 9567-9576.
8. (a) J. Malthete, A. Collet, Inversion of the cyclotribenzylene cone in a columnar mesophase: a potential way to ferroelectric materials, J. Am. Chem. Soc., 1987, 109 (24), 7544-7545; (b) D. Felder, B. Heinrich, D. Guillon, J. F. Nicoud, J. F Nierengarten, A liquid crystalline supermolecular xomplex of C60 with a cyclotriveratrylene derivative, Chem. Eur. J., 2000, 6 (19), 3501-3507; (c) H. Zimmermann, V. Bader, R. Poupko, E. J. Wachtel, Z. Luz, Mesomorphism, isomerization, and dynamics in a new series of pyramadic Liquid Crystals, J. Am. Chem. Soc., 2002, 124 (51), 15286-15301.
9. A. Collet., J. Jacques, M. Cesario, J. Guilhem, J. Chem. Soc., Perkin Trans. 1, 1981, 1630
10. (a) J. Canceill, L. Lacombe, A. Collet, Analytical optical resolution of bromochlorofluoromethane by enantioselective inclusion into a tailor-made “cryptophane” and determination of its maximum rotation, J. Am. Chem. Soc., 1985, 107 (24), 6993-6996; (b) Z. L. Zhong, A. Ikeda, S. Shinkai, S. Sakamoto, K. Yamaguchi, Creation of novel chiral cryptophanes by a self-assembling method utilizing a pyridyl-Pd (II) interaction, Org. Lett., 2001, 3 (7), 1085-1087; (c) E. T. Rump, D. T. S Rijkers, H. W. Hilbers, P. G. Groot; R. M. J. Liskamp,. Cyclotriveratrylene (CTV) as a new chiral triacid scaffold capable of inducing triple helix formation of collagen peptides containing either a native sequence or Pro-Hyp-Gly repeats, Chem. Eur. J., 2002, 8 (20), 4613-4621.
11. A. Collet, Cyclotriveratrylenes and cryptophanes, Tetrahedron, 1987, 43 (24), 5725-5759.
12. B. Umezama, O. Hoshino, H. Hara, K. Ohyama, S. Mitsubayashi, Chemistry of cyclotriveratrylene. Ⅰ. Formation of cyclotriveratrylene from veratrylamine N-Tosylate, Chem. Pharm. Bull., 1969, 17 (11), 2240-2244..
13. J. Bosch, J. Canals; R .Granados, Productos de acopaminto del cloruro de 3,4,5-trimetoxibencilmagnesio, Anal. Quim., 1976, 72, 709-712.
14. M. SaImón, A. Cabrera, N. Zavala, G.. Espinosa-Pérez, J. Cárdenas, R. Gavi?o, R. Cruz, X-ray crystal structure and 1H-NMR chiral shift reagent study of a crown trimer, J. Chem. Crystallogr., 1995, 25 (11), 759-763.
15. P. Lesot, D. Merlet, M. Sarfati, J. Courtieu, H. Zimmermann, Z. Luz, Enatiomeric and enantiotopic analysis of cone-shaped compounds with C3 and C3v symmetry using NMR spectroscopy in chiral anisotropic solvents, J. Am. Chem. Soc., 2002, 124 (34), 10071-10082.
16. M. Salmón, N. Zavala, M .Martínez, R. Cruz, Cyclic and linear oligomerization reaction of 3,4,5-trimethoxybenzyl alcohol with a Bentonite-clay, Tetrahedron Lett., 1994, 35 (32), 5797-5800.
17. W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals. London, 1997, 4th ED.
2. P. N. Solis, A. G. Ravelo, A. G. Gonzalez, M. P. Gupta, J. D. Phillipson, Boiacitve anthraquinone glycosides from Picramnia Antidesma SSP. Fessonia, Phytochemistry, 1995, 38 (2), 477-480.
3. J. Kinjo, T. Ikeda, K. Watanbe, T. Nohara, An anthraquinone glycoside from Cassia Angustifolia leaves, Phytochemistry, 1994, 37 (6), 1685-1685.
4. A. A. El-Gamal, K. Takeya, H. Itokawa, A. F. Halm, M. M. Amer, H. A. Saad, S. A. Awad, Anthraquinone from Galium Sinaicum, Phytochemistry, 1995, 40 (1), 245-251.
5. C. N. Lin, B. L. Wei, Anthroquinone and naphthalene glycosides from Rhamus Nakaharai, Phytochemistry, 1993, 33 (4), 905-908.
6. I. Kubo, Y. Murai, I. Soediro, S. Soetaino, S. Sastrodihardjo, Cytotoxic anthraquinone from Rheum Pulmatum, Phytochemistry, 1992, 31 (3), 1063-1065.
7. M. Kazmi, A. Malik, S. Hameed, N. Akhtar, S. N. Ali, An anthraquinone derivative from Cassia Italica, Phytochemistry, 1994, 36 (3), 761-763.
8. P. A. Cohen, G. H. N. Towers, The anthroquinones of Heterodermia Obscurata, Phytochemistry, 1995, 40 (3), 911-915.
9. D. V. Banthorpe, J. J. White, Novel anthraquinones from undifferentiated cell cultures of Galium Verum, Phytochemistry, 1995, 38 (1), 107-111.
10. Z. Zhou, S. H. Jiang, D. Y. Zhu, L. Z Lin, G. A. Cordell, Anthraquinones from Knoxia Valerianoides, Phytochemistry, 1994, 36 (3), 765-768.
11. E. Dagne, A. Yenesew, S. Asmellash, S. Demissew, S. Mav, Anthraquinones, pre-anthraquinones and isoeleutherol in the roots of Aloe species, Phytochemistry, 1994, 35 (2), 401-406.
12. L. F. Van Staden, S. E. Drewes, Knipholone from bulbine latifolia and bulbinefrutescens, Phytochemistry, 1994, 35 (3), 685-686.
13. J. Koyama, J. Ogura, K. Tagahara, Anthraquinones of Galium Spurium, Phytochemistry, 1993, 33 (6), 1540-1542.
14. B. L. Wei, C. N. Lin, S. J. Won, Nakahalene and cytotoxic priciples of Formosan Rhamnus species, J. Nat. Prod., 1992, 55 (7), 967-969.
15. P. A. Cohen, G. H. N. Towers, Anthrawuinones and phenanthroper; enequinones from Nephroma Laevigtum, J. Nat. Prod., 1995, 58 (4), 520-526.
16. J. Koyama, T. Ogura, K. Tagahara, T. Konoshima, M. Kozuka, Two naphthoquinones from Rubia Cordifola, Phytochemistry, 1992, 31 (8), 2907-2908.
17. X. Z. Lu, W. H. Xu, H. Naoki, Anthraquinones from Salvia Przewalskii, Phytochemistry, 1992, 31 (2), 708-709.
18. B. Barba, J. G. Dlaz, W. Herz, Anthraquinones and other constituents of two Senna species, Phytochemistry, 1992, 31 (12), 4734-4735.
19. T. K. Yadav, S. B. Kalidar, Alquinone: An anthraquinone from Cassia alata, Planta Med., 1994, 60, 601-603.
20. B. Jaki, J. Heilman, O. Sticher, New antibacterical metabolites from the cyanobacterium Nostoc commune (EAWAG 122b), J. Nat. Prod., 2000, 63 (9), 1283-1285.
21. M. Morimoto, K. Tanimoto, A. Sakatani, K. Komai, Antifeedant activity of an anthraquinone aldehyde in Galium aparine L. against Spodoptera litura F., Phytochemistry, 2002, 60, 163-166.
22. B. L. Wei, C. M. Lu, L. T. Tsao, J. P. Wang, C. N. Lin, In vitro anti-inflammatory effects of quercetin 3-O-methyl ether and other constituents from Rhamnus species, Planta Med., 2001, 67, 745-747.
23. J. Koyama, T. Okatani, K. Tagahara, I. Kouno, H. Irie, Anthraquinones of Damnacanthus Indicus, Phytochemistry, 1992, 31 (2), 709-710.
24. G. Bringmann, D. Menche, M. Bezabih, B. M. Abegaz, R. Kaminsky, Antiplasmodial activity of Knipholone and related natural phenylanthraquinones,Planta Med., 1999, 65, 757-758.
25. M. A. Qhotasokane-Lusunzi, P. Karuso, Secondary metabolitics from basotho medicinal plants.Ⅰ. Bulbine narcissifola, J. Nat. Prod., 2001, 64, 1368-1372.
26. G. Brauers, R. A. Edrada, R. Ebel, P. Proksch, V. Wray, A. Berg, U. Gr?fe, C. Sch?chtele, F. Totzke, Anthraquinones and betaenone derivatives from the sponge-associated fugus Microphaeropsis species: novel inhibitors of protein kinases, J. Nat. Prod., 2000, 63 (6), 739-745.
27. 向兰,郑俊华,果德安,寇晋萍,范国强,段豫萍,秦晨,窄叶大黄醌类化学成分研究,中草药,2001,32(5),395-396。
28. A. R. Bilia, A. W. Yusuf, A. Braca, A. Keita, I. Morelli, New prenylated anthraquinones and xanthones from Vismia guineesis, J. Nat. Prod., 2000, 63, 16-21.
29. 邱峰,徐金钟,段文娟,曲戈霞,王乃利,姚新生,红葱中的新化学成分,高等学校化学学报,2005,26(11),2057-2060。
30. D. Carins, E. Michalitsi, T. C. Jenkins, S. P. Mackay, Molecular modeling and cytotoxicity of substituted anthraquinones as inhibitors human telomerase, Bioorganic & medicinal chemistry, 2002, 803-807.
31. J. Koyama, I. Morita, K. Tagakazu, M. Ogata, T. Mukainaka, H. Tokuda, H. Nishino, Inhibtory effects of anthraquinones and bianthraquinones on Epstein-Barr virus activation, Cancer Lett., 2001, 170, 15-18.
32. G. Z. Jin, Y. J. You, Y. Kim, N. H. Nam, B. Z. Ahn, Esters of chlorambucil with 2-substituted 1,4-dihydroxy-9,10-anthraquinones as multifunctional anticancer agents, Eur. J. Med. Chem.,2001, 36, 361-366.
33. 王定勇,唐菖蒲和飞蛾藤的化学成分研究,中国科学院博士学位论文,2003。
34. M. Chrysayi-Tokousbalides, M. A. Kastanias, Cynodontin: A fungal metabolite with antifungal properties, J. Agric. Food Chem., 2003, 51 (17), 4920-4923.
35. G. Meazza, F. E. Dayan, D. E. Wedge, Activity of quinones on Colletotrichum species, J. Agric. Food Chem., 2003, 51 (13), 3824-3828.
36. B. S. Park, J. R. Kim, S. E. Lee, K. S. Kim, G. R. Takeoka, Y. J. Ahn, J. H. Kim,
Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria, J. Agric. Food Chem., 2005, 53 (4), 1152-1157.
37. K. Mitura, H. Kikuzaki, N. Nakatani, Antioxidant activity of chemical components from Sage (Salvia officinalis L.) and Thyme (Thymus vulgaris L.) measured by the oil stability index method, J. Agric. Food Chem., 2002, 50 (7), 1845-1851.
38. N. V. S. Ramakrishna, K. H. S. Swamy, E. K. S. V. Kumar, M. M. S. Kushwaha, S. Kota, M. Raman, S. D Tare, S. K. Deshmukh, D. Schummer, M. Kurz, H. Kogler, Patents PTC/EP99/04127 and WO 99-67408 A1.
39. L. Vertesy, M. Kurz, E. F. Paulus, D. Schummer, P. Hammann, J. Antibiot., 2001, 54, 354-363。
40. B. L. Wei, S. H. Wu, M. I. Chung, S. J. Won, C. N. Lin, Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives, Eur. J. Med. Chem., 2000, 35, 1089-1098.
41. W. Werner, U. Gr?fe, W. Ihn, D. Tresselt, S. Winter, E. Paulus, Synthesis of Tolypocladin and Isotolypocladin, Tetrahedron, 1997, 53 (1), 109-118.
42. K. S. Kim, M. W. Spatz, F. Johnson, Anthracyclines and related substancesⅠ. A new Friedel-Crafts alkylation reaction using 3-Bromophthalides. Efficient synthesis of islandicin, Tetrahedron Lett., 1979, 20 (4), 331-334.
43. M. L. Patil, H. B. Borate, D. E. Ponde, V. H. Deshpande, Total synthesis of (±)-brasiliquinone B, Tetrahedron, 2002, 58, 6615-6620.
44. Mahesh L. Patil, Hanumant B. Borate, Datta E. Ponde, Baburao M. Bhawal, Visum H. Deshpande, First total synthesis of (±)-brasiliquinone B, Tetrahedron Lett., 1999, 40, 4437-4438.
45. D. L. Boger, J. Hong, M. Hikota, M. Ishida, Total synthesis of Phomazarin, J. Am. Chem. Soc., 1999, 121, 2471-2477.
46. B. Caron, P. Brassard, An integrated approach to the synthesis of contiguously substituted xanthopurpurins, pachybasins and purpurrins, Tetrahedron, 1993, 49(4), 771-784.
47. M. Gill, P. M. Morgan, J. M. White, J. Yu, Pigments of fungi. XLⅦ cardinalic acid, a new anthraquinone carboxylic acid from the New Zealand Dermocybe cardinalis and synthesis and X-ray crystal structure of methyl 1,7,8-tri-o-methylcardinalate, Aust. J. chem., 1998, 51, 213-218.
48. K. Krohn, J. Micheel, M. Zukowski, Total synthesis of angucyclines. Part 15: a short synthesis of (±)-6-deoxybrasiliquinone B, Tetrahedron, 2000, 56, 4753-4758.
49. D. W. Cameron, C. Corn, G. I. Feutrill, Chemistry of the coccoidea Ⅱsynthesis of ceroalblinic acid, Aust. J. Chem., 1981, 34, 1945.
50. J. M. Pérez, P. López-Alvarado, C. Avenda?o, J. C. Menéndez, Hetero Diels-Alder reactions of 1-acetylamino- and 1-dimethylamino-1-azadienes with benzoquinones, Tetrahedron, 2000, 56, 1561-1567.
51. K. Kobayashi, M. Uchida, S. Watanabe, A. Takanohashi, M. Tanmatsu, O. Morikawa, H. Konishi, Synthesis of 1-amino- and 1-hydroxy-9, 10-anthraquinone derivative based on reaction sequences between 2-acetyl-1,4-naphthraquinone and enamines, Tetrhedron Lett., 2000, 41, 2381-2384.
52. G. A. Kraus, H. Cho, S. Crowley, B. Roth, H. Sugimoto, S. Prugh; Phthalide annulation: the synthesis of kalafungin, pachybasin and chrysophanol. J. Org. Chem., 1983, 48 (20), 3439-3444.
53. M. Braun, A regioselective synthesis of daunomycinone and related anthracyclinones, Tetrahedron, 1984, 40 (22), 4585-4591.
54. S. O. de Silva, M. Watanabe, V. Snieckus, General route to anthraquinone natural products via directed metalation of N,N-diethylbenzamides, J. Org. Chem., 1979, 44 (26), 4802-4808.
55. K. C. Nicolaou, J. L.Gross, M. A. Kerr, R. H. Lemus, K.Ikeda, K. Ohe, Synthesis of the anthraquinone framework of Dynemicin A, Angew. Chem. Int. Ed. Engl., 1994, 33 (7), 781-783.
56. H. Zhao, E. Biehl, Preparation of naturally occurring anthraquinone using arynereaction, J. Nat. Prod., 1995, 58 (12), 1970-1974.
57. F. Kaiser, L. Schwink, J. Velder, H. G. Schmalz, Studies towards the total synthesis of mumubaistatin: synthesis of highly substituted benzophenone and anthraquinone building block, Tetrahedron, 2003, 59, 3201-3217.
58. C. A. Townsend, S. G. Davis, S. B. Christensen, J. C. Link, C. P. Lewis, Methoxymethyl-directed aryl metalation. A total synthesis of (±)-averufin, J. Am. Chem. Soc., 1981, 103, 6885-6888.
59. M. Watanabe, E. Shinoda, Y. Shimizu, S. Furukawa, Synthesis of bostrycoidin via lithiation of tertiary nicotinamide, Tetrahedron, 1987, 43 (22), 5281-5286.
60. D. L. Boger, J. Hong, M. Hikota, M. Ishida, Total synthesis of phomazarin, J. Am. Chem. Soc., 1999, 121, 2471-2477.
61. B. J. Whitlock, H. W. Whitlock, Regiospecific synthesis of islandicin methyl ether, J. Org. Chem., 1980, 45 (1), 12-15.
62. N. R. Ayyangar, J. Sci. Industr. Res., 1961, 20B, 493.
63. A. Kalogerakis, U. Groth, Synthesis of the benzo[а]anthraquinone core of angucylinone antibiotics, Org. Lett., 2003, 5 (6), 843-844.
64. F. E. McDonald, H. Y. H. Zhu, C. R. Holmquist,Rhodium-catalyzed alkyne cyclotrimerization strategies for C-aryl glycoside synthesis, J. Am. Chem. Soc., 1995; 117 (24); 6605-6606.
1. J. R. Vane, Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs, Nature (New Biol.), 1971, 231, 232-235.
2. 王庆利,盛春元,赵桂宏,新型非甾体抗炎药 COX-2 选择性抑制剂的研究及应用前景,中国药房,2001, 12 (5), 304-305。
3. J. L. Masferrer, K. Seibert, B. S. Zwefei, The induction and suppression of prostaglandin H2 synthase (cyclooxygenase) in human monocytes, J. Biol. Chem., 1990, 265, 16737-16741.
4. W. Xie, J. G. Chipman, D. L. Robert, Expreesion of a mitogen-resposive gene ecoding prostaglandin synthase is regulated by mRNA splicing, Proc. Natl. Acad. Sci. USA, 1991, 88, 2692-2699.
5. I. Siegle,T. Klein,J. T. Packman, Expression of cyclooxygenase-1 and cyclooxygenase-2 in human synovial tissue : Diferential elevation of cyclooxygenase-2 in inflammatoryjoint diseases, Arthritis Rheum, 1998,4l, l22-.
6. J. P. Famay, In vitro and in vivo pharmacological evidence of selective cyclooxygenase-2 inhibition by nime sulide:an overview, Influmm. Res,1997, 46, 437.
7. J. A. Mitchell, P. Alarasereenot, J. R. Vane, Pharmacological and biochemical demonstration of the role cyclooxygenase-2 in inflammation and pain, Proc. Natl. Acad. Sci. USA, 1993, 90, 11693-11697.
8. G. A. Fitzgerald, Coxibs and cardiovascular disease, N. Engl. J. Med., 2004, 351(17), 1709 - 1711.
9. K. Shinmura, X. L. Tang, Y. Wang, Cyclooxygenase-2 mediates the cardioprotective effects of the late phase of ischemic preconditioning in conscious rabbits, Proc. Natl. Acad. Sci. USA, 2000, 97 (18), 10197 - 10202.
10. S. D. Solomon, J. J. MeMurray, M. A. Pfeffer, Cardiovascular risk associated with celecoxib in a clinical trial for colorectal adenoma prevention, N. Engl. J. Med., 2005, 352, 1071-1080.
11. D. Mukherjee, E. J. Topol, COX-2: where are we in 2003? Cardiovascular risk and COX-2 inhibitors, Arthritis. Res. Ther., 2003, 5 (1), 8 - 11.
12. D. Y. Wang, Q. Ye, B. G. Li, G. L. Zhang, A new anthraquinone from Gladiolus gandavensis, Nat. Prod. Res., 2003, 17 (5), 365-368.
13. D. Y. Wang, Q. Ye, B. G. Li, G. L. Zhang, New anthraquinones from Gladiolus gandavensis, J. Asian Prod. Res., 2003, 5 (4), 297-301.
14. B. Chen, D. Y. Wang, Q. Ye, B. G. Li, G. L. Zhang, Anthraquinones from Gladiolus gandavensis, J. Asian Prod. Res., 2003, 5 (4), 297-301.
15. T. Danishesky, T. Kitahara, A useful diene for Diels-Alder reaction, J. Am. Chem. Soc., 1974, 96 (25), 7807-7808.
16. J. W. Patterson, The Alder-Rickert reaction in a synthesis of m-chlorophenols and 4-chloromycophenolic acid, J. Org. Chem., 1995, 60 (3), 560-563.
17. A. Barbero, F. J. Pulido, Isoxazoles as latent siloxybutadienes: an easy entry to polyfunctionalized benzene systems via Diels-Alder reaction with acetylenes, Synthesis, 2004, 3, 401-404.
18. C. Pulgarin, J. Gunzinger, R. Tabacchi, Synthèse de l’ériodermine, Helv. Chim. Acta., 1985, 68, 945-948.
19. A. A. Birkbeck, M. V. Sargent, J. A. Elix, The atructure of the lichen depsidones fulgidin and isofulgidin, Aust. J. Chem., 1990, 43, 419-425.
20. J. A. Elix, K. L. Gaul, H. Jiang, The structure and synthesis of some minor xanthones from the lichen rinodina thiomela, Aust. J. Chem.,1993, 46, 95-110.
21. M. L. Patil, H. B. Borate, D. E. Ponde, V. H. Deshpande, Total synthesis of (±)-brasiliquinone B, Tetrahedron, 2002, 58, 6615-6620.
22. J. P. Hwang, G. K. S. Prakash, G. A. Olah, Trifuoromethanesulfonic acid catalyzed novel Friedel-Crafts acylation of aromatics with methyl benzoate, Tetrahedron, 2000, 56, 7199-7203.
23. A. G. Schultz, S. A. Hardinger, Photochemical and acid-catalyzed dienone-phenol rearrangement. The effect of substituents on the regioselectivity of 1,4-sigmatrtropic rearrangements of the type A intermediate, J. Org. Chem., 1991, 56, 1105-1111.
24. V. Snieckus, Directed ortho metalation. Tertary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics, Chem. Rev., 1990, 90 (6), 879 – 933.
25. J. J. Court, D. J. Hlasta, Ortho versus adjacent-benzylic directed lithiations of substituted N,N-diethylbenzamides, Tetrahedron Lett., 1996, 37 (9), 1335-1338.
26. J. Clayden, J. H. Pink, N. Westlund, F. X. Wilson, Controlling the regioselectivity of lithiation using kinetic isotope effects: deuterium as protecting group forcarbon, Tetrahedton Lett., 1998, 39, 8377-8380.
27. D. Tilly, S. S. Samanta, F. Faigl, J. Mortier, Combined directed ortho metalation–intrqmolecular Friedel-Crafts connections. Regiospecific route to 1-substituted fluoren-9-ones, Tetrahedron Lett., 2002, 43, 8347-8350.
28. F. Gohier, J. Mortier, ortho-Metalation of unprotected 3-bromo and 3-chlorobenzoic acids with hindered lithium dialkylamides, J. Org. Chem., 2003, 68 (5), 2030-2033.
29. J. Kristensen, M. Lysén, P. Vedso, M. Begtrup, Synthesis of ortho substituted arylboronic ester by in situ trapping of unstable lithio intermediates, Org. Lett., 2001, 3 (10), 1435-1437.
30. W. A. Carroll, X. L. Zhang, Competitve ortho metalation effects: the kinetic and thermodynamic lithiation of 3- (tert-butoxycarbonyl)amino-4-carbomethoxythiophene, Tetrahedron Lett., 1997, 38(15), 2637-2640.
31. J. G.. Allen, S. J. Danishefsky, The total synthesis of (±)-rishirilide, J. Am. Chem. Soc., 2001, 123 (2), 351-352.
32. S. Dey, D. Mal, Total synthesis of BE-23254, a chlorinated angucycline antibiotic, Tetrahedron Lett., 2005, 46, 5483-5486.
33. L. Cleaver, J. A. Croft, E. Ritchie, W. C. Taylor, Chemical studies of the protaceae. Ⅸ. Synthesis of 5-alkylresorcinols from aliphatic precursors, Aust. J. Chem., 1976, 29, 1989-1995.
34. C. Pulgarin, R. Tabacchi, Synthèse de l’acide décarboxythamnolique, Helv. Chim.Acta., 1988, 71, 876-880.
35. C. Pulgarin, J. Gunzinger, R. Tabacchi, Synthèse des pseudocyphellarins A et B, deux depsides du lichen pseudocyphellaria endochrysea, Helv. Chim. Acta., 1985, 68, 1948-1951.
36. J. A. Elix, R. Naidu, G. Thor, Cyclofraphin, a new depdidone from the lichen catarraphia dictyolaca, Aust. J. Chem., 1995, 48, 635-649.
37. W. E. Wymann, R. Davis, J. W. Pattterson, J. R. Pfister, Selective alkylations of certain phenolic and enolic functions with lithium carbonate halide, Syn. Commun., 1988, 18 (12), 1379-1384.
38. A. J. Pearson, P. R. Brun, Studies on the synthesis of aryl ethers using areno-manganese chemistry, J. Org. Chem., 1991, 56 (25), 7092-7097.
39. C. F. Carvalho, A. V. Russo, M. V. Sargent, Boron trichloride as a selective demethylation agent for hindered ethers: a synthesis of the phytoalexins A and B pyrufran, a synthesis of tripopmehtylleprolomin and its demethylation, Aust. J. Chem., 1985, 777-792.
40. 景崤壁,任新锋,彭坤,武同兴,潘鑫复,选择性去甲醚化反应——3,5-二甲氧基 4-羟基苯甲酸甲酯的新合成方法,兰州大学学报(自然科学版),2001,37(3),78-79。
41. P. Lesot, D. Merlet, M. Sarfati, J. Courtieu, H. Zimmermann, Z. Luz, Enatiomeric and enantiotopic analysis of cone-shaped compounds with C3 and C3v symmetry using NMR spectroscopy in chiral anisotropic solvents, J. Am. Chem. Soc., 2002, 124 (34), 10071-10082.
42. M. Salmón, N. Zavala, M .Martínez, R. Cruz, Cyclic and linear oligomerization reaction of 3,4,5-trimethoxybenzyl alcohol with a Bentonite-clay, Tetrahedron Lett., 1994, 35 (32), 5797-5800.
43. G. Keum, H. J. Lim, S. B. Kang, Y. Kim, B. Y. Chung, Indium catalyzed Friedel-Crafts benzylation of aromatic compounds with benzyl halides, Bull. Korean Chem. Soc., 2000, 21 (8), 809-812.
44. G. A. Olah, J. A. Olah, T. Ohyama, Friedel-Crafts alkylation of anisole and its comparison with toluene. Predominant ortho-para substitution under kinetic conditions and the effect of thermodynamic isomerizations, J. Am. Chem. Soc., 1984, 106 (18), 5284-5290.
45. T. Yamato, M. Fukumoto, N. Sakaue, T. Furusawa, M. Tashiro, A new route for the synthesis of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene using Friedel-Crafts intramolecular cyclobenzylation, Synthesis, 1991, 9, 699-700.
46. S. Urgaonkar, H. S. La Pierre, I. Meir, H. Lund, D. RayChaudhuri, J. T. Shaw, Synthesis of antimicrobial natural products targeting FtsZ: (±)-dichamanetin and (±)-2’’’-hydroxy-5’’-benzylisouvarinol-B, Org. Lett. 2005, 7 (25), 5609-5612.
47. J. A. Ruell, E. De Clercq, C. Pannecouque, M. Witvrouw, T. L. Stup, J. A. Turpin, R. W. Buckheit, M. Cushman, Synthesis of anti-HIV activity of cosalane analogues with substituted benzoic acid rings attached to the pharmacophore through methylene and amide linkers, J. Org. Chem., 1999, 64 (16), 5858-5866.
48. T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa, Scandim (Ⅲ) triflate catalyzed Friedel-Crafts alkylation with benzyl and allyl alcohols, Synlett, 1996,557-559.
49. A. Ishii, O. Kotera, T. Saeki, K. Mikami, Trimethylsilyl bis(trifluoromethanesulfonyl)amide as a effective catalyst for Friedlel-Crafts alkylation reaction, Synlett, 1997, 6, 1145-1146.
50. T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa, Scandium(III) triflate-catalyzed Friedel-Crafts alkylation reactions, J. Org. Chem., 1997, 62 (20), 6997-7005.
51. T. Miyai, Y. Onishi, A. Baba, Novel reductive Friedel-Crafts alkylation of aromatics catalyzed by indium compounds: chemoselective utilization of carbonyl moieties as alkylating reagents, Tetrahedron, 1999, 55, 1017-1026.
52. T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa, Scandium(III) trifluoromethanesulfonate-catalysed reductive Friedel–Crafts benzylation of aromatic compounds using arenecarbaldehydes and propane-1,3-diol, Chem. Commun., 1996, 20, 2345-2346.
53. S. Fukuzawa, T. Tsuchimoto, K. Tobita, T. Hiyama, Superacid-catalyzed reductive Friedel-Crafts reaction of arenas using arenecarbaldehyde acetals, J. Org. Chem., 1997, 62, 151-156.
54. W. L. F.Armarego, D. D. Perrin,. Purification of Laboratory Chemicals. London, 1997, 4th ED.
1. Robinson, G.M. A Reaction of Homopiperonyl and of Homoveratryl Alcohols, J. Chem. Soc. 1915, 107, 267-276.
2. (a) A. S. Lindsey, The structure of cyclotriveratrylene (10,15-dihydro-2,3,7,8,12,13-hexamethoxy-5H-tribenzo[a,d,g]cyclononene) and related compounds, J. Chem. Soc., 1965, 1685-1691. (b) A. S. Lindsey, Cyclotroveratrylene and related compounds, Chem. Ind. (Lond), 1963, 823-824.
3. H. Erdtman, F. Haglid, R. Ryhage, Macrocyclic condensation products of veratrole and resorcinol, Acta. Chem. Scand., 1964, 18, 1249-1254.
4. A. Goldup, A. B. Morrison, G. W. Smith, The structure of cycloveratril, J. Chem. Soc., 1965, 3864-3866.
5. J. A. Hyatt, E. N. Duesler, D. Y. Curtin, I. C.Paul, Stoichiometric Inclusion compounds of cyclotriveratrylene and cyclotricatechylene with small neutral molecules. X-ray crystal structure of cyclotricatechylene di-2-propanolate. J. Org. Chem., 1980. 45 (25), 5074-5079.
6. (a) A. Collet, G. Gottarelli, Circular dichroism spectrum of C3-cyclotriguaiacylene after ionization of the phenolic groups. experimental approach to the magic angle region in C3-cyclotriveratrylene derivative, J. Am. Chem. Soc., 1982, 104 (25), 7383-7384; (b) A. Collet, G.. Gottarelli, The circular dichroism and absolute configuration of C3-chiral derivatives of cyclotriveratrylene, J. Am. Chem. Soc., 1981, 103 (1), 204-205.
7. (a) R. Ahmad, A. Franken, J. D. Kennedy, M. J.Hardie, Group 1 coordination chains and hexagonal networks of host cyclotriveratrylene with halogenated monocarbaborane anions, Chem. Eur. J., 2004, 10, 2190-219; (b) A. Arduini, F. Calzavacca, D. Demuru, A. Pochini, A. Secchi, Synthesis of cavity extended cyclotriveratrylenes, J. Org. Chem., 2004, 69 (4), 1386-1388; (c) T. Brotin, J. P. Dutasta, Xe@cryptophane complexes with C2 symmetry: synthesis and investigations by 129Xe NMR of the consequences of the size of the host cavity for xenon encapsulation, Eur. J. Org. Chem., 2003, 973-984; (d) D. S. Bohle, D. J. Stasko, Salicylaldiminato derivatives of cyclotriveratrylene: Flexible strategy for new rim-mMetalated CTV complexes, Inorg. Chem., 2000, 39, 5768-5770; (e) J. F. Nierengarten, L. Oswald, J. F. Eckert, J. F. Nicoud, N. Armaroli, Complexation of fullerenes with dendritic cyclotriveratrylene derivatives, Tetrahedron Lett., 1999, 40, 5681-5684; (f) M. J. Hardie, P. D.Godfrey, C. L. Raston, Self-assembly of grid and helical hydrogen-bonded arrays incorporating bowl-shaped receptor sites that bind globular molecules, Chem. Eur. J., 1999, 5 (6), 1828-1833; (g) K. T. Holman, M. M. Halihan, S. S. Jurisson, J. L. Atwood, R. S. Burkhalter, A. R. Mitchell, J. W. Steed, Inclusion of neutral and anionic guests within the cavity of π-metalated cyclotriveratrylenes, J. Am. Chem. Soc., 1996, 118 (40), 9567-9576.
8. (a) J. Malthete, A. Collet, Inversion of the cyclotribenzylene cone in a columnar mesophase: a potential way to ferroelectric materials, J. Am. Chem. Soc., 1987, 109 (24), 7544-7545; (b) D. Felder, B. Heinrich, D. Guillon, J. F. Nicoud, J. F Nierengarten, A liquid crystalline supermolecular xomplex of C60 with a cyclotriveratrylene derivative, Chem. Eur. J., 2000, 6 (19), 3501-3507; (c) H. Zimmermann, V. Bader, R. Poupko, E. J. Wachtel, Z. Luz, Mesomorphism, isomerization, and dynamics in a new series of pyramadic Liquid Crystals, J. Am. Chem. Soc., 2002, 124 (51), 15286-15301.
9. A. Collet., J. Jacques, M. Cesario, J. Guilhem, J. Chem. Soc., Perkin Trans. 1, 1981, 1630
10. (a) J. Canceill, L. Lacombe, A. Collet, Analytical optical resolution of bromochlorofluoromethane by enantioselective inclusion into a tailor-made “cryptophane” and determination of its maximum rotation, J. Am. Chem. Soc., 1985, 107 (24), 6993-6996; (b) Z. L. Zhong, A. Ikeda, S. Shinkai, S. Sakamoto, K. Yamaguchi, Creation of novel chiral cryptophanes by a self-assembling method utilizing a pyridyl-Pd (II) interaction, Org. Lett., 2001, 3 (7), 1085-1087; (c) E. T. Rump, D. T. S Rijkers, H. W. Hilbers, P. G. Groot; R. M. J. Liskamp,. Cyclotriveratrylene (CTV) as a new chiral triacid scaffold capable of inducing triple helix formation of collagen peptides containing either a native sequence or Pro-Hyp-Gly repeats, Chem. Eur. J., 2002, 8 (20), 4613-4621.
11. A. Collet, Cyclotriveratrylenes and cryptophanes, Tetrahedron, 1987, 43 (24), 5725-5759.
12. B. Umezama, O. Hoshino, H. Hara, K. Ohyama, S. Mitsubayashi, Chemistry of cyclotriveratrylene. Ⅰ. Formation of cyclotriveratrylene from veratrylamine N-Tosylate, Chem. Pharm. Bull., 1969, 17 (11), 2240-2244..
13. J. Bosch, J. Canals; R .Granados, Productos de acopaminto del cloruro de 3,4,5-trimetoxibencilmagnesio, Anal. Quim., 1976, 72, 709-712.
14. M. SaImón, A. Cabrera, N. Zavala, G.. Espinosa-Pérez, J. Cárdenas, R. Gavi?o, R. Cruz, X-ray crystal structure and 1H-NMR chiral shift reagent study of a crown trimer, J. Chem. Crystallogr., 1995, 25 (11), 759-763.
15. P. Lesot, D. Merlet, M. Sarfati, J. Courtieu, H. Zimmermann, Z. Luz, Enatiomeric and enantiotopic analysis of cone-shaped compounds with C3 and C3v symmetry using NMR spectroscopy in chiral anisotropic solvents, J. Am. Chem. Soc., 2002, 124 (34), 10071-10082.
16. M. Salmón, N. Zavala, M .Martínez, R. Cruz, Cyclic and linear oligomerization reaction of 3,4,5-trimethoxybenzyl alcohol with a Bentonite-clay, Tetrahedron Lett., 1994, 35 (32), 5797-5800.
17. W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals. London, 1997, 4th ED.