Dragonamide和Leucamide A的全合成研究
|
摘要
论文完成了海洋天然化合物Dragonamide的化学全合成,并纠正了文献中的构型错误。同时对海洋天然化合物Leucamide A的化学合成进行了研究。
设计了Dragonamide的全合成路线,由四肽片段A.15和片段(R)-2-甲基-7-炔-辛酸,A.28组成。将片段A.15的氨基保护基脱去后,以BOPCl为偶合试剂,与A.28连接起来,得到A.30。将A.30的羧基保护基脱除后,以PyBOP为偶合试剂,与氨气反应,得到Dragonamide,收率为10.9%。
四肽片段A.15的合成是以L-苯丙氨酸和L-撷氨酸为起始原料,利用邻硝基苯磺酰基作为氨基的保护基团,叔丁酯作为羧基的保护基团,碘甲烷作为烷基化试剂,酰氯作为偶合试剂而完成,收率为32.5%。
(R)-2-甲基-7-炔-辛酸,A.28的合成是以1.5-戊二醇为起始原料,以苄基完成单保护后,经Swern氧化反应得到醛,再与wittig试剂反应,增长碳链。选择性加氢后,水解脱去酯基后与Evans手性助剂反应得到手性前体。以NaHMDSA为碱,在-78℃下,进行立体选择性烷基化反应,构造手性中心。脱去手性助剂,以重氮甲烷甲酯化,脱去苄基,得到醇。Swern氧化后,与Ohira-Bestmann试剂反应,在保持手性中心的前提下,得到炔基,脱去甲酯后,得到A.28,收率为17.1%,e.e.值大于99%。
经过与标准谱图的比较,得出文献中分子构型错误的结论,即A.28中手性的构型应为S。合成相应的(S)-2-甲基-7-炔-辛酸后,重复前述步骤,得到构型正确的目标分子Dragonamide,构型为SSSSS(文献中构型为RSSSS),总收率为1.86%。
设计了Leucamide A的全合成路线,由中间体噁唑-亮氨酸-脯氨酸B.12,甲基噁唑衍生物B.20和苯并三唑衍生物B.24组成并完成了对它们的合成。
片段B.12是由二肽片段B.10和噁唑衍生物B.6偶合得到。二肽片段B.10以L-亮氨酸和L-脯氨酸为起始原料,以叔丁氧羰基为氨基保护基团,甲酯为羧基保护基,以DCC为偶合试剂得到,收率为56.7%。噁唑衍生物B.6利用L-丝氨酸和L-丙氨酸为起始原料,得到二肽片段B.4后,经Burgess试剂关环,BrCCl_3和DBU脱氢得到,收率为46.8%。
B.20以L-丝氨酸和L-苏氨酸为起始原料,得到二肽B.17,经过Dess-MartinPeriodinane氧化和三苯基膦与碘关环,生成甲基噁唑B.19,收率为36.5%。B.19脱去保护基后,得到B.20。
硫代撷氨酸的活化中间体B.24以L-撷氨酸为起始原料,保护氨基后,利用氯甲酸异丁酯作为偶合试剂,与邻苯二胺反应,硫代后,利用亚硝酸关环得到。
Dragonamide, an oceanic nature material, was total synthesized in the paper.And fragments of Leucamide A, an oceanic nature material too, were synthesized.
Synthesis route to Dragonamide was designed. The molecule was made up withTetrapeptide A.15 and (R)-2-methyl-7-alkyl-octyl acid, A.28. They were coupledusing BOPCl as coupling reagent to give A.30. After cleavage of the t-butyl ester ofA.30, Dragonamide was achieved by activation with PyBOP and treatment withammonia in a yield of 10.9%.
Tetrapeptide A.15 was prepared from L-Phe and L-Val in a yield of 32.5%, withO-nitrobenzenesulfonyl group and t-Butyl group as protecting groups.
(R)-2-methyl-7-alkyl-octyl acid, A.28 was prepared from 1,5-pentanediol. Aftermonoprotection and Swern oxidation, aldehyde was got. Then it reacted with wittigreagent. After selective hydrogenation and hydrolyzation, the intermediate wascoupled with chiral auxiliary. Then alkylation of stereoselective was completed withNAHMDSA and MeI at -78 ℃ . Chiral auxiliary was removed, followed byesterification with diazomethane, hydrogenation and Swern oxidation to give anotheraldehyde. It was converted alkyne using the Ohira-Bestmann reagent.(R)-2-methyl-7-alkyl-octyl acid, A.28 was got after saponification in a yield of 17.1%and e.e. beyond 99%.
Due to its NMR data and optical rotation data could not match them in reference,it was found that structure of dragonamide was wrong. Then(S)-2-methyl-7-alkyl-octyl acid was prepared using exactly the same procedure. Andcorrect Dragonamide was synthesized at finally in a total yield of 1.86%, andstructure was SSSSS not RSSSS.
Synthesis route to Leucamide A was designed. The molecule was made up withB.12, B.20 and B.24 which were prepared in the paper.
B.12 was given from coupling after removing protecting groups of B.10 and B.6.Dipeptide B.10 was obtained from L-Leu and L-Pro in a yield of 56.7%. In a similarway Dipeptide B.4 was got from L-Ser and L-Ala. After cyclodehydration withBurgess reagent and dehydrogenation with BrCCl3&DBU, the oxazole B.6 wasprepared in a yield of 46.8%.
B.20 was obtained after removing protacting group of B.19. Dipeptide B.17 wasobtained from L-Ser and L-Thr through similar way, followed by oxidation with
Dess-Martin Periodinane and cyclodehydration with PPh3&I2 to givemethyloxazole B.19 in a yield of 36.5%.Activted intermediate B.24 was prepared from L-Val through coupling witho-diaminobenzene ,sulfuration and cyclodehydration.
设计了Dragonamide的全合成路线,由四肽片段A.15和片段(R)-2-甲基-7-炔-辛酸,A.28组成。将片段A.15的氨基保护基脱去后,以BOPCl为偶合试剂,与A.28连接起来,得到A.30。将A.30的羧基保护基脱除后,以PyBOP为偶合试剂,与氨气反应,得到Dragonamide,收率为10.9%。
四肽片段A.15的合成是以L-苯丙氨酸和L-撷氨酸为起始原料,利用邻硝基苯磺酰基作为氨基的保护基团,叔丁酯作为羧基的保护基团,碘甲烷作为烷基化试剂,酰氯作为偶合试剂而完成,收率为32.5%。
(R)-2-甲基-7-炔-辛酸,A.28的合成是以1.5-戊二醇为起始原料,以苄基完成单保护后,经Swern氧化反应得到醛,再与wittig试剂反应,增长碳链。选择性加氢后,水解脱去酯基后与Evans手性助剂反应得到手性前体。以NaHMDSA为碱,在-78℃下,进行立体选择性烷基化反应,构造手性中心。脱去手性助剂,以重氮甲烷甲酯化,脱去苄基,得到醇。Swern氧化后,与Ohira-Bestmann试剂反应,在保持手性中心的前提下,得到炔基,脱去甲酯后,得到A.28,收率为17.1%,e.e.值大于99%。
经过与标准谱图的比较,得出文献中分子构型错误的结论,即A.28中手性的构型应为S。合成相应的(S)-2-甲基-7-炔-辛酸后,重复前述步骤,得到构型正确的目标分子Dragonamide,构型为SSSSS(文献中构型为RSSSS),总收率为1.86%。
设计了Leucamide A的全合成路线,由中间体噁唑-亮氨酸-脯氨酸B.12,甲基噁唑衍生物B.20和苯并三唑衍生物B.24组成并完成了对它们的合成。
片段B.12是由二肽片段B.10和噁唑衍生物B.6偶合得到。二肽片段B.10以L-亮氨酸和L-脯氨酸为起始原料,以叔丁氧羰基为氨基保护基团,甲酯为羧基保护基,以DCC为偶合试剂得到,收率为56.7%。噁唑衍生物B.6利用L-丝氨酸和L-丙氨酸为起始原料,得到二肽片段B.4后,经Burgess试剂关环,BrCCl_3和DBU脱氢得到,收率为46.8%。
B.20以L-丝氨酸和L-苏氨酸为起始原料,得到二肽B.17,经过Dess-MartinPeriodinane氧化和三苯基膦与碘关环,生成甲基噁唑B.19,收率为36.5%。B.19脱去保护基后,得到B.20。
硫代撷氨酸的活化中间体B.24以L-撷氨酸为起始原料,保护氨基后,利用氯甲酸异丁酯作为偶合试剂,与邻苯二胺反应,硫代后,利用亚硝酸关环得到。
Dragonamide, an oceanic nature material, was total synthesized in the paper.And fragments of Leucamide A, an oceanic nature material too, were synthesized.
Synthesis route to Dragonamide was designed. The molecule was made up withTetrapeptide A.15 and (R)-2-methyl-7-alkyl-octyl acid, A.28. They were coupledusing BOPCl as coupling reagent to give A.30. After cleavage of the t-butyl ester ofA.30, Dragonamide was achieved by activation with PyBOP and treatment withammonia in a yield of 10.9%.
Tetrapeptide A.15 was prepared from L-Phe and L-Val in a yield of 32.5%, withO-nitrobenzenesulfonyl group and t-Butyl group as protecting groups.
(R)-2-methyl-7-alkyl-octyl acid, A.28 was prepared from 1,5-pentanediol. Aftermonoprotection and Swern oxidation, aldehyde was got. Then it reacted with wittigreagent. After selective hydrogenation and hydrolyzation, the intermediate wascoupled with chiral auxiliary. Then alkylation of stereoselective was completed withNAHMDSA and MeI at -78 ℃ . Chiral auxiliary was removed, followed byesterification with diazomethane, hydrogenation and Swern oxidation to give anotheraldehyde. It was converted alkyne using the Ohira-Bestmann reagent.(R)-2-methyl-7-alkyl-octyl acid, A.28 was got after saponification in a yield of 17.1%and e.e. beyond 99%.
Due to its NMR data and optical rotation data could not match them in reference,it was found that structure of dragonamide was wrong. Then(S)-2-methyl-7-alkyl-octyl acid was prepared using exactly the same procedure. Andcorrect Dragonamide was synthesized at finally in a total yield of 1.86%, andstructure was SSSSS not RSSSS.
Synthesis route to Leucamide A was designed. The molecule was made up withB.12, B.20 and B.24 which were prepared in the paper.
B.12 was given from coupling after removing protecting groups of B.10 and B.6.Dipeptide B.10 was obtained from L-Leu and L-Pro in a yield of 56.7%. In a similarway Dipeptide B.4 was got from L-Ser and L-Ala. After cyclodehydration withBurgess reagent and dehydrogenation with BrCCl3&DBU, the oxazole B.6 wasprepared in a yield of 46.8%.
B.20 was obtained after removing protacting group of B.19. Dipeptide B.17 wasobtained from L-Ser and L-Thr through similar way, followed by oxidation with
Dess-Martin Periodinane and cyclodehydration with PPh3&I2 to givemethyloxazole B.19 in a yield of 36.5%.Activted intermediate B.24 was prepared from L-Val through coupling witho-diaminobenzene ,sulfuration and cyclodehydration.
引文
[1] 郭保章, 董德沛, 化学史简明教程. 北京: 北京师范大学出版社, 1985, p317-p323
[2] K.C.Nicolaou, Dionisios Vourloumis, Nicolas Winssinger, The Art and Science of Total Synthesis. Angew. Chem. Int. Ed. 2000, 39, 44-122
[3] R. B. Woodward, Gurbakhsh Singh, The Synthesis Of Patulin. J. Am. Chem. Soc. 1950, 72, 1428-1428
[4] R. B. Woodward, A. A. Patchett, D. H. R. Barton, The Synthesis Of Lanostenol. J. Am. Chem. Soc. 1954, 76, 2852-2853
[5] R. B. Woodward, W. E. Doering, The Total Synthesis Of Quinine. J. Am. Chem. Soc. 1944, 66, 849-849
[6] R. B. Woodward, F. Sondheimer, The Total Synthesis of Steroids. J. Am. Chem. Soc. 1952, 74, 4223-4251
[7] R. B. Woodward, E. Logisch, Asymmetric total synthesis of erythromcin. 1. Synthesis of an erythronolide A secoacid derivative via asymmetric induction. J. Am. Chem. Soc. 1981, 103, 3210-3213
[8] E. J. Corey, D. Y. Gin, R. S. Kania, Enantioselective Total Synthesis of Ecteinascidin 743. J. Am. Chem. Soc. 1996, 118, 9202-9203
[9] E. J. Corey, M. M. Mehrotra, Total synthesis of (+-)-clavulones. J. Am. Chem. Soc. 1984, 106, 3384-3384
[10] E. J. Corey, D. C. Ha, Total synthesis of venustatriol. Tetrahedron Lett. 1988, 29, 3171-3174
[11] E. J. Corey, L. O. Weigel, A. R. Chamberlin, Total synthesis of maytansine. J. Am. Chem. Soc. 1980, 102, 6613-6615
[12] G. Stork, F. West, H. Y. Lee, The Total Synthesis of a Natural Cardenolide: (+)-Digitoxigenin. J. Am. Chem. Soc. 1996, 118, 10660-10661
[13] G. Stork, T. Takahashi, I. Kawamoto, Total synthesis of prostaglandin F2.alpha. by chirality transfer from D-glucose. J. Am. Chem. Soc. 1978, 100, 8272-8273
[14] G. Stork, J. J. La Clair, P. Spargo, Stereocontrolled Synthesis of (±)-12a-Deoxytetracycline. J. Am. Chem. Soc. 1996, 118, 5304-5305
[15] A.Eschenmoser, C. E. Wintner, Natural product synthesis and vitamin B12. Science 1977, 196, 1410-1420
[16] A.Eschenmoser, Chemical Etiology of Nucleic Acid Structure. Science 1999, 284, 2118-2124
[17] M. Beier, F. Reck, A.Eschenmoser, Chemical Etiology of Nucleic Acid Structure: Comparing Pentopyranosyl-(2' 4') Oligonucleotides with RNA. Science 1999, 283, 699-703
[18] D.H.R.Barton, J. M. Beaton, L.E. Geller, A New Photochemical Reaction. J. Am. Chem. Soc. 1960, 82, 2640-2641
[19] D.H.R.Barton, J. M. Beaton, A Synthesis of Aldosterone Acetate. J. Am. Chem. Soc. 1961, 83, 4083-4089
[20] 易杨华, 李玲, 海洋药物研究展望与对策. 第二军医大学学报 2001, 22(9), 801-802
[21] 张兴德, 刘汉清, 海洋药物研究进展. 南京中医药大学学报 2003, 19(2), 126-128
[22] 王艳, 周培根, 戚晓玉, 海洋生物中毒素的研究进展. 上海水产大学学报2002, 11(3), 283-288
[23] George R. Pettit, Yoshiaki Kamano, Cherry L. Herald, Isolation of dolastatins 10–15 from the marine mollusc dolabella auricularia. Tetrahedron 1993, 49, 9151-9170
[24] George R. Pettit, Sheo Bux Singh, Fiona Hogan, Antineoplastic agents. Part 189. The absolute configuration and synthesis of natural (-)-dolastatin 10. J. Am. Chem. Soc. 1989, 111, 5463-5465
[25] Poncet J., Busquet M., Roux F., Synthesis and Biological Activity of Chimeric Structures Derived from the Cytotoxic Natural Compounds Dolastatin 10 and Dolastatin 15. J. Med. Chem. 1998, 41(9), 1524-1530
[26] George R. Pettit, Yoshiaki Kamano, Claude Dufresne, Isolation and structure of the cytostatic linear depsipeptide dolastatin 15. J. Org. Chem. 1989, 54, 6005-6006
[27] George R. Pettit, Delbert L. Herald, Sheo Bux Singh, Antineoplastic agents. 220. Synthesis of natural (-)-dolastatin 15. J. Am. Chem. Soc. 1991, 113, 6692-6693
[28] George R. Pettit, Yoshiaki Kamano, Cherry L. Herald, Structure of bryostatin. 4. An important antineoplastic constituent of geographically diverse Bugula neritina (Bryozoa). J. Am. Chem. Soc. 1984, 106, 6768-6771
[29] 关美君, 林文翰, 丁源, 海洋药物--二十一世纪中国药学研究的新热点. 中国海洋药物 2001, 79, 1-5
[30] 黄建设, 龙丽娟, 海洋天然产物及其生理活性的研究进展. 海洋通报 2001, 20(4), 83-91
[31] 林厚文, 易杨华, 姚新生, 南中国海总合草苔虫中一个新的抗肿瘤化合物:Bryostatin19. 中国海洋药物 1998, 17(1), 1
[32] Sakai R. Rinehart, K. kishore, Structure-activity relationships of didemnis. J. Med. Chem. 1996, 39(14), 2819
[33] 姚新生, 易杨华, 汤海峰等, 海洋抗肿瘤物质研究概况与展望. 药学服务与研究 2002, 2(1), 7-16
[34] Lindel T., Jensen P. R., Fenical W., Eleutherobin, a New Cytotoxin that Mimics Paclitaxel (Taxol) by Stabilizing Microtubules. J. Am. Chem. Soc. 1997, 119, 8744-8745
[35] Sarath P. Gunasekera, Malika Gunasekera, Ross E. Longley, Discodermolide: a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissolute. J. Org. Chem. 1990, 55, 4912-4915
[36] Amy E. Wright, Dorilyn A. Forleo, Geewananda P. Gunawardana, Antitumor tetrahydroisoquinoline alkaloids from the colonial ascidian Ecteinascidia turbinate. J. Org. Chem. 1990, 55, 4508-4512
[37] Kenneth L. Rinehart, Tom G. Holt, Nancy L. Fregeau, Ecteinascidins 729, 743, 745, 759A, 759B, and 770: potent antitumor agents from the Caribbean tunicate Ecteinascidia turbinate. J. Org. Chem. 1990, 55, 4512-4515
[38] Gerwick W. H., Proteau P. J., Nagle D. G. , Structure of Curacin A, a Novel Antimitotic, Antiproliferative and Brine Shrimp Toxic Natural Product from the Marine Cyanobacterium Lyngbya majuscula. J. Org. Chem. 1994, 59, 1243-1245
[39] James C Muir, Gerald Pattenden, Tao Ye, A concise total synthesis of (+)-curacin A, a novel cyclopropyl-substituted thiazoline from the cyanobacterium Lyngbya majuscula . Tetrahedron Lett. 1998, 39, 2861-2864
[40] 刘凤云、李赏、周艳荣等,海洋生物毒素的药物开发前景,生物技术通讯2002,13(5),392-394
[41] Satoshi S., Koji M., Kyosuke T., Amino acid sequence of two sea anemone toxins from Anthopjeura fuscovides. Toxicon 1987, 26, 639
[42] 郑星明,王益寿,海洋资源药物开发现状与前景. 上海化工 1999,24(1), 4-5
[43] Michael Z. Hoemann, Konstantinos A. Agrios, Jeffrey Aubé, Total synthesis of curacin A . Tetrahedron Lett. 1996, 37, 953-956
[44] Michael Z. Hoemann, Konstantinos A. Agrios and Jeffrey Aubé, Total synthesis of (+)-curacin A, a marine cytotoxic agent. Tetrahedron 1997, 53, 11087-11098
[45] Wipf P., Xu W., Total Synthesis of the Antimitotic Marine Natural Product (+)-Curacin A. J. Org. Chem. 1996, 61, 6556-6562
[46] Jing-Yu Lai, Jurong Yu, Belew Mekonnen, Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula . Tetrahedron Lett. 1996, 37, 7167-7170
[47] James C. Muir, Gerald Pattenden, Tao Ye, A Concise Total Synthesis of (+)-curacin A, a Novel Cyclopropyl-substituded Thiazoline from the Cyanobacterium Lyngbya majuscula. Tetrahedron Lett. 1998, 39, 2861-2864
[48] Luesch H., Yoshida W. Y., Moore R. E., Isolation, Structure Determination, and Biological Activity of Lyngbyabellin A from the Marine Cyanobacterium Lyngbya majuscula. J. Nat. Prod. 2000, 63, 611-615
[49] Yokokawa F., Sameshima H., Shioiri T., Total synthesis of lyngbyabellin A, a potent cytotoxic metabolite from the marine cyanobacterium Lyngbya majuscula. Tetrahedron 2001, 42, 4171-4174
[50] Xu Z. S., Peng Y. G., Ye T, International Forum On Pharmaceutical Techonology(2002), 70
[51] Clausen K., Thorsen M., Lawesson S. O., Studies on Amino Acids and Peptide-I: Synthesis of N-Benzyloxycarbonylendo-thiodipeptide ester, Tetrahedron 1981, 37, 3635-3639
[52] Wipf P., Fritch P. C., Synthesis of Peptide Thiazolines from β-hydroxythioamides. An Investigation of Racemization in Cyclodehydration Protocals. Tetrahedron Lett. 1994, 35, 5397-5440
[53] Atkins G. M., Burgess E. M. The Reaction of an N-sulfonylamine inner salt. J. Am. Chem. Soc. 1968, 90, 4744-4745
[54] Boden C. D., Pattenden G., Ye T. The Synthesis of Optically active Thiazoline and Thiazole Derived Peptides from N-protected-amino Acids. Synlett. 1995, 417-419
[55] Shalaby M. A., Grote C. W., Rapoport H. Thiopeptide Synthesis: α-Amino Thionoacid Derivatives of Nitrobenzotrizole as Thioacylating Agents. J. Org. Chem. 1996, 61, 9045-9048
[56] Luesch H., Pangilinan R., YoShida W. Y., Pitipeptolides A and B, New Cyclodepsipeptides from the Marine Cyanobacterium Lyngbya majuscula. J.Nat.Prod. 2001,64,304~307
[57] Xu Z. S., Peng Y. G., Ye T, International Forum On Pharmaceutical Techonology (2002), 70
[58] Paul Lloyd-Williams, Fernando albericio, Ernest Giralt. Chemical Approaches to the Synthesis of Peptides and Proteins, New York: CRC Press, 1997, p95-104
[59] Gergory A. Grant, Synthetic Peptides, New York: Oxford University Press, 2002, p93-219
[60] M. Bodanszky, A. Bodanszky, The Practice of Peptide Synthesis, New York: Springer-Verlag, 1984, p7-85, p151-195, p87-150
[61] M. Bodanszky, Principles of Peptide Synthesis, New York: Springer-Verlag, 1984, p59-107, p158-195
[62] Philip J. Kocieński, Protecting Groups, Thieme, 1994, p185-244, p21-87, p118-151
[63] Theodora W. Greene, Protecting Groups in Organic Synthesis, New York: John Wiley & Sons, Inc. 1980, p309-406, p224-277, p10-143
[64] 黄维生, 多肽合成, 北京: 科学出版社, 12-56, p102-p149
[65] Oliver Seitz, New Protecting Group Strategies for the Solid-Phase Synthesis and Modification of Peptides, Oligonucleotides, and Oligosaccharides. Angew. Chem. Int. Ed. 1998, 37(22), 3109-3111
[66] Tohru Fukuyama, Mui Cheung, Chung-Kuang Jow, 2,4-Dinitrobenzenesulfonamides: A Simple and Practical method for the Preparation of a Variety of Secondary Amines and Diamines. Tetrahedron Lett. 1997, 38(33), 5831-5834
[67] James R. Vaughan, Jr. Ruth L. Osato, The Preparation of Peptides Using Mixed Carbonic-Carboxylic Acid Anhydrides. J. Am. Chem. Soc. 1952, 74, 676-678
[68] George Washington Anderson, Joan E. Zimmerman, Francis M. Callahan, Reinvestigation of the mixed carbonic anhydride method of peptide synthesis. J. Am. Chem. Soc. 1967, 89, 5012-5017
[69] So-Yeop Han, Young-Ah Kim, Recent Development of Peptide Coupling Reagents in Organic Synthesis, Tetrahedron 2004, 60, 2447-2467
[70] Jorge I. Jiménez, Paul J. Scheuer, New Lipopeptides from the Caribbean Cyanobacterium Lyngbya majuscula, J. Nat. Prod. 2001, 64, 200-203
[71] Reese M. T., Gulavita N. K., Nakao Y., Kulolide: A Cytotoxic Depsipeptide from a Cephalaspidean Mollusk, Philinopsis speciosa. J. Am. Chem. Soc. 1996, 118, 11081-11084
[72] Nakao Y., Yoshida W. Y., Szabo C. M., More Peptides and Other Diverse Constituents of the Marine Mollusk Philinopsis speciosa. J. Org. Chem. 1998, 63, 3272-3280
[73] George R. Pettit, Jun-Ping Xu, Fiona Hogan, Isolation and Structure of Dolastatin 17. Heterocycles 1998, 47(1), 491-496
[74] Jaime Rodríguez, Rogelio Fernández, Emilio Qui?oá, Onchidin: a cytotoxic depsipeptide with C2 symmetry from a marine mollusk. Tetrahedron Lett. 1994, 35, 9239-9242
[75] Luesch H., Yoshida W. Y., Moore R. E., Apramides A-G, Novel Lipopeptides from the Marine Cyanobacterium Lyngbya majuscula. J. Nat. Prod. 2000, 63, 1106-1112
[76] Stefan Kehraus, Gabriele M. K?nig, Anthony D. Wright, Leucamide A: A New Cytotoxic Heptapeptide from the Australian Sponge Leucetta microraphis, J. Org. Chem. 2002, 67, 4989-4992
[77] David A. Evans, Leester D. Wu, John J. M. Wiener, A General Method for the Synthesis of Enantiomerically Pure β-Substituted, β-Amino Acids through α-Substituted Succinic Acid Derivatives. J. Org. Chem. 1999, 64, 6411-6417
[78] Peter Wipf, Yuntae Kim, Paul C. Fritch. Total Synthesis and Structure Assignment of the Antitumor Antibiotic Aranorosin. J. Org. Chem. 1993, 58, 7195-1203
[79] Richard E. Taylor, Yue Chen, Total Synthesis of Epothilones B and D. Organic Letters 2001, 3(14), 2221-2224
[80] Carl P. Decicco, David J. Nelson, Ronald L. Corbett, Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of a-Trifluoromet hanesulfonat e Substituted Esters. J. Org. Chem. 1996, 60, 4782-4785
[81] Marco Lerm, Hans-Joachim Gais, Kejun Cheng, Asymmetric Synthesis of the Highly Potent Anti-Metastatic Prostacyclin Analogue Cicaprost and Its Isomer Isocicaprost. J. Am. Chem. Soc. 2003, 125, 9653-9667
[82] D. A. Evans, M. D. Ennis, D. J. Mathre, Asymmetric Alkylation Reactions of Chiral Imide Enolates. A Practical Approach to the Enantioselective Synthesis of a-Substituted Carboxylic Acid Derivatives. J. Am. Chem. Soc. 1982, 104, 1737-1739
[83] Michael G. Organ, Yaroslav V. Bilokin, Svetoslav Bratovanov, Approach toward the Total Synthesis of Orevactaene. 2. Convergent and Stereoselective Synthesis of the C18-C31 Domain of Orevactaene. Evidence for the Relative Configuration of the Side Chain, J. Org. Chem. 2002, 67, 5176-5183
[84] Jennifer L. Belelie, J. Michael Chong, Stereoselective Reactions of Acyclic Allylic Phosphates with Organocopper Reagents, J. Org. Chem. 2001, 66, 5552-5555
[85] Victor Garcia-Ruiz, Simon Woodward, On the absolute stereochemistry of (-)-4-alkylnonan-2-ones. Tetrahedron: Asymmetry 2002, 13, 2177–2180
[86] David A. Evans, Mark T. Bilodeau, Todd C. Somers, Enantioselective Michael Reactions. Diastereoselective Reactions of Chlorotitanium Enolates of Chiral N-Acyloxazolidinones with Representative Electrophilic Olefins. J. Org. Chem. 1991, 56, 5750-5752
[87] Khuong Mai, Ghanshyam Patil, Alkylsiyl Cyanides as Silyating Reagents. J. Org. Chem. 1986, 51, 3545-3548
[88] Guy Solladié, Francoise Colobert Colobert, Chakib Kala?, Stereoselective Synthesis of All-trans Methyl Substiuted Polyenes by Reductive Elimination and Application to the Synthesis of All-trans 3-Methyl-nona-2,4,6-trienol. Tetrahedron Lett. 2000, 41, 4197-4200
[89] Gary A. Molander, Jan Antoinette C. Romero, Christopher P. Corrette, Hydrosilylation of Alkynlsilanes Utilizing Organlanthanide and Group 3 Metallocene Complexes. Journal of Oraganmetallic Chemistry 2002, 647, 225-235
[90] Ei-ichi Negishi, Larry D. Boardman, Hiroyuki Sawada, Novel Cyclialkylation Reactions of (ω-Halo-1-alkenyl)metal Derivatives. Synthetic Scope and Methanism. J. Am. Chem. Soc. 1988, 110, 5383-5396
[91] Scott E. Schaus, Jonas Branalt, Eric N. Jacobsen, Total Synthesis of Muconin by Efficient Assembly of Chiral Building Blocks. J. Org. Chem. 1998, 63, 4876-4877
[92] Ulrich Berlage, Jürgen Schmidt, Ulrike Peters, A formal total synthesis of (±)-strigol. Tetrahedron Lett. 1987, 28, 3091-3094
[93] E. J. Corey, Ryu Nagata, Synthesis of three new dehydroarachidonic acid derivatives and their oxidation by soybean lipoxygenase. Tetrahedron Lett. 1987, 28, 5391-5394
[94] Carl P. Decicco, Paul Grover, Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A. J. Org. Chem. 1996, 61, 3534-3541
[95] Stacie S. Canan Koch, A. Richard Chamberlin, Enantioselective Preparation of 8-Alkyl-y-butyrolactones from Functionalized Ketene Dithioacetals, J. Org. Chem. 1993, 58, 2725-2737
[96] Serge David, Annie Thieffry, Conversion of One Hydroxy Group in a Diol to a Phenyl Ether with Triphenylbismuth Diacetate, a New Glycol Reaction Showing Strong Axial Preference in Six-Membered Rings. J. Org. Chem. 1983, 48, 441-447
[97] Patrick G. McDougal, Joseph G. Rico, Young-Im Oh, A Convenient Procedure for the Monosilylation of Symmetric 1,n –Diols. J. Org. Chem. 1986, 51, 3388-3390
[98] Kanji Omura, Daniel Swern, Oxidation of Alcohols by “Activated” Dimethyl Sulfoxide. A Preparative, Steric and Mechanistic Study. Tetrahedron 1978, 34, 1651-1660
[99] James A. Marshall, Marc W. Andersen, Synthesis of 12-, 14-, and 16-Membered Propargylic Alcohols through Lewis Acid-Promoted Ene Cyclization. J. Org. Chem. 1993, 58, 3912-3918
[100] Steven Wolff, Bhaskar Rao Venepalli, Clifford F. George, Some Thermal and Photochemical Reactions of [ 4.4.4.5 ] Fenestranes. J. Am. Chem. Soc. 1988, 110, 6785-6790
[101] B. C. Hamper, α-Acetylenic Esters From α-Acylmethylenephosphoranes: Ethyl 4,4,4-Trifluorotetrolate, Organic Syntheses CV 9, 436
[102] Robert W. Lang, Hans-Jürgen Hansen, α-Allenic Esters from α-Phosphoranylidene Esters and Acid Chlorides: Ethyl 2,3-Pentadienoate. Organic Syntheses CV 7, 232
[103] Andrew D. Abell, Kathryn B. Morris, J. Christopher Litten, Synthesis and Deprotection of [ 1-( Et hoxycarbony1)-4-[ (diphenylmet hoxy )carbonyl]-1-met hyl-2-oxobutyl]-triphenylphosphonium Chloride: A Key Intermediate in the Wittig Reaction between a Cyclic Anhydride and a Stabilized Ylide. J. Org. Chem. 1990, 55, 5217-5221
[104] Gregory R. Cook, Lars G. Beholz, John R. Stille, Construction of Hydroxylated Alkaloids (f )-Mannonolactam, (f )-Deoxymannojirimycin, and (f ) -Prosopinine through aza-Annulation. J. Org. Chem. 1994, 59, 3575-3584
[105] Wolfgang Barth, Leo A. Paquette, Synthesis of a representative cis/trans pair of 4,5-disubstituted cyclopentenyllithium reagents. J. Org. Chem. 1985, 50, 2438-2443
[106] Franciszek Kazmierczak, Paul Helquist, Synthesis of the branched nine-carbon unit of the type A streptogramins and other antibiotics. J. Org. Chem. 1989, 54, 3988-3992
[107] Lanchi Vo, James Ciula, Owen W. Gooding, Chemical Development on the Chiral Auxiliary (S)-4-(Phenylmethyl)-2-oxazolidinone Utilizing Automated Synthesis and DoE. Organic Process Research & Development 2003, 7, 514-520
[108] David A. Evans, Thomas C. B&ton, Jon A. Ellman, Contrasteric Carboximide Hydroolysis with Lithium Hydroperoxide. Tetrahedron Lett. 1987, 28(49), 6141-6144
[109] D. A. Evans, J. Bartroli, T. L. Shih, Enantioselective Aldol Condensations. 2. Erythro-Selective Chiral Aldol Condensations via Boron Enolates. J. Am. Chem. Soc. 1981, 103, 2127-2129
[110] Th. J. de Boer, H. J. Backer, Diazomethane. Organic Syntheses CV 4, 250
[111] Th. J. de Boer, H. J. Backer, p-Tolylsulfonylmethylnitrosamide. Organic Syntheses CV 4, 943
[112] David R. Williams, David L. Brown, John W. Benbow, Studies of Stemona Alkaloids. Total Synthesis of (+)-Croomine. J. Am. Chem. Soc. 1989, 111, 1923-1925
[113] Stephan Muller, Bemd Liepold, Gerald J. Roth, An Improved One-pot Procedure for the Synthesis of Alkynes from Aldehydes. Synlett. 1996, 521-522
[114] K. C. Nicolaou, F. Murphy, S. Barluenga, Total Synthesis of the Novel Immunosuppressant Sanglifehrin A. J. Am. Chem. Soc. 2000, 122, 3830-3838
[115] William R. F. Goundry, Jack E. Baldwin, Victor Lee, Total synthesis of cytotoxic sponge alkaloids hachijodines F and G. Tetrahedron 2003, 59, 1719–1729
[116] Miyuki Ishizaki, Kazuhiko Iwahara, Yuka Niimi, Investigation of the synthesis of angular tricyclic compounds by intramolecular Pauson±Khand reaction of exo-and endo-cyclic enynes. Tetrahedron 2001, 57, 2729-2738;Yoshitaka Matsushima, Hiroaki Itoh, Takuya Nakayama, Enantioselective total synthesis of vicenistatin, a novel 20-membered macrocyclic lactam antitumor antibiotic. J. Chem. Soc., Perkin Trans. 2002, 1, 949–958
[117] Harris, Christopher, John, Beta-Ketophosphonates, US, WO03027129, 20030403
[118] Tohru Fukuyama, Chung-kuang Jow, Mui Cheung, 2-and 4-Nitrobenzenesulfonamides: Exceptionally Versatile Means for Preparation of Secondary Amines and Protection of Amines. Tetrahedron Lett. 1995, 36(36), 6373-6374
[119] Edwin Vedejs, Chutima Kongkittingam, Solution-Phase Synthesis of a Hindered N-Methylated Tetrapeptide Using Bts-Protected Amino Acid Chlorides: Efficient Coupling and Methylation Steps Allow Purification by Extraction. J. Org. Chem. 2000, 65, 2309-2318
[120] W. Russell Bowman, Daniel R. Coghlan, A Facile Method for the N-Alkylation of α-Amino Esters. Tetrahedron 1997, 53(46), 15787-15798
[121] Engel K-H., Lipase-catalyzed enantioselective esterification of 2-methylalkanoic acids. Tetrahedron: Asymmetry 1991, 2, 165-168
[122] Berglund P., Holmquist M., Hedenstr?m E., 2-Methylalkanoic acids resolved by esterification catalysed by lipase from Candida rugosa: Alcohol chain length and enantioselectivity. Tetrahedron: Asymmetry 1993, 4, 1869-1878
[123] Hu J., Miller M. J., Total Synthesis of a Mycobactin S, a Siderophore and Growth Promoter of Mycobacterium Smegmatis, and Determination of its Growth Inhibitory Activity against Mycobacterium tuberculosis. J. Am. Chem. Soc. 1997, 119, 3462-3468
[124] Prakash Raman, Suzanne S. Stokes, Yvonne M. Angell, Methods to Circumvent a Difficult Coupling in the Solid-Phase Synthesis of Cyclosporine Analogues. J. Org. Chem. 1998, 63, 5734-5735
[125] Injae Shin, Kisoo Park, Solution-Phase Synthesis of Aminooxy Peptoids in the C to N and N to C Directions. Organic Lett. 2002, 4(6), 869-872
[126] Jaume Farràs, Xavier Ginesta, Pedro Romea, β3-Amino acids by nucleophilic ring-opening of N-nosyl aziridines. Tetrahedron 2001, 57, 7665-7674
[127] Stephen C. Miller, Thomas S. Scanlan, oNBS-SPPS: A New Method for Solid-Phase Peptide Synthesis. J. Am. Chem. Soc. 1998, 120, 2690-2691
[128] Juan Cabre, Antonio Luis Palomo, New Experimental Strategies in Amide Synthesis using N,N-Bis[2-oxo-3-oxazolidinyl]phosphorodiamidic Chloride. Synthesis. 1984, 413-417
[129] Yvonne M. Angell, Carlos Garcia-Echeverria, aniel H. Rich, Comparative Studies of the Coupling of N-Methylated, Sterically Hindered mino Acids During Solid-Phase Peptide Synthesis. Tetrahedron Lett. 1994, 35(33), 5981-5984
[130] Rdger D. Tung, Daniel H. Rich, Bis(2-oxo-3-oxazolidinyl)phosphinic Chloride as a Coupling Reagent for N-Alkyl Amino Acids. J. Am. Chem. Soc. 1985, 107, 4342-4343
[131] J. Diago-Meseguer, A. L. Palomo, A New Reagent for Activating Carboxyl Groups;Preparation and Reactions of N,N-Bis[2-oxo-3-oxazolidinyl] phosphorodiamidic Chloride. Synthesis. 1980, 547-551
[132] Estelle Dumez, John S. Snaith, Richard F. W. Jackson, Synthesis of Marcocylic, Protential Protease Inhibitiors Using a Generic Scaffold, J. Org. Chem. 2002, 67, 4882-4892
[133] Luiz C. Dias, Andrea A. Ferreira, Gaspar Diaz, Short Total Synthesis of Aspartyl Protease Inhibitors L-685,434, L-682,679 and L-685,458, Synlett. 2002, (11), 1845-1849
[134] Rodney L. Parsons, Clayton H. Heathcock, Total Synthesis of Mirabazole B, Tetrahedron Lett. 1994, 35(9), 1383-1384
[135] Alam Dal Pozzo, Laura Muzi, Maurizio, etc., Synthesis of RGD Analogues Containing α-Tfm-Arginine as Potential Fibrinogen Receptor Antagonists, Tetrahedron 1998, 54, 6019-6028
[136] Bryan C. N. M. Jones, John C. Drach, Jiri Zemlicka, etc., (+-)-N9-(2-(Hydroxymethyl)spiro[3.3]hept-6-yl)adenine. The First Biologically Active Saturated Analog of Adenallene with Axial Dissymmetry. J. Org. Chem. 1995, 60, 6277-6280
[137] Azzouz BenCheikh, Leslie E. Craine, Jiri Zemlicka, etc., Synthesis of Racemic 6'β-Hydroxyaristeromycin. A Hydroxycarbocyclic Analogue of Adenosine, J. Org. Chem. 1988, 53(5), 929~936
[138] M. Ashraf Shalaby, Christopher W. Grote, Henry Rapoport, Thiopeptide Synthesis. r-Amino Thionoacid Derivatives of Nitrobenzotriazole as Thioacylating Agents. J. Org. Chem. 1996, 61, 9045-9048
[139] Paul J. Stevenson, Alan B. Treacy, Mark Nieuwenhuyzen, Preparation of Dess–Martin periodinane—the role of themorphology of 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide precursor. J. Chem. Soc., Perkin Trans. 2 1997, 589-591
[140] Stephanie D. Meyer, Stuart L. Schreiber, Acceleration of the Dess-Martin Oxidation by Water. J. Org. Chem. 1994, 59, 7549-7552
[141] Robert E. Ireland, Longbin Liu, An Improved Procedure for the Preparation of the Dess-Martin Periodinane, J. Org. Chem. 1993, 58, 2899
[142] Edward M. Burgess, Harold R. Penton, Conversion of primary Alcohols to urethanes via the inner salt of methyl(carboxysulfamoyl)triethylammonium hydroxide:methyl n-hexylcarbamate. Organic Syntheses CV 6, 788
[143] Peter Wipf, Srikanth Venkatraman, An Improved Protocol for Azole Synthesis with PEG-Supported Burgess Reagent. Tetrahedron Lett. 1996, 37(27), 4659-4662
[144] M. Ashraf Shalaby, enry Rapoport, A General and Efficient Route to Thionoesters via Thionoacyl Nitrobenzotriazoles. J. Org. Chem. 1999, 64, 1065-1070
[2] K.C.Nicolaou, Dionisios Vourloumis, Nicolas Winssinger, The Art and Science of Total Synthesis. Angew. Chem. Int. Ed. 2000, 39, 44-122
[3] R. B. Woodward, Gurbakhsh Singh, The Synthesis Of Patulin. J. Am. Chem. Soc. 1950, 72, 1428-1428
[4] R. B. Woodward, A. A. Patchett, D. H. R. Barton, The Synthesis Of Lanostenol. J. Am. Chem. Soc. 1954, 76, 2852-2853
[5] R. B. Woodward, W. E. Doering, The Total Synthesis Of Quinine. J. Am. Chem. Soc. 1944, 66, 849-849
[6] R. B. Woodward, F. Sondheimer, The Total Synthesis of Steroids. J. Am. Chem. Soc. 1952, 74, 4223-4251
[7] R. B. Woodward, E. Logisch, Asymmetric total synthesis of erythromcin. 1. Synthesis of an erythronolide A secoacid derivative via asymmetric induction. J. Am. Chem. Soc. 1981, 103, 3210-3213
[8] E. J. Corey, D. Y. Gin, R. S. Kania, Enantioselective Total Synthesis of Ecteinascidin 743. J. Am. Chem. Soc. 1996, 118, 9202-9203
[9] E. J. Corey, M. M. Mehrotra, Total synthesis of (+-)-clavulones. J. Am. Chem. Soc. 1984, 106, 3384-3384
[10] E. J. Corey, D. C. Ha, Total synthesis of venustatriol. Tetrahedron Lett. 1988, 29, 3171-3174
[11] E. J. Corey, L. O. Weigel, A. R. Chamberlin, Total synthesis of maytansine. J. Am. Chem. Soc. 1980, 102, 6613-6615
[12] G. Stork, F. West, H. Y. Lee, The Total Synthesis of a Natural Cardenolide: (+)-Digitoxigenin. J. Am. Chem. Soc. 1996, 118, 10660-10661
[13] G. Stork, T. Takahashi, I. Kawamoto, Total synthesis of prostaglandin F2.alpha. by chirality transfer from D-glucose. J. Am. Chem. Soc. 1978, 100, 8272-8273
[14] G. Stork, J. J. La Clair, P. Spargo, Stereocontrolled Synthesis of (±)-12a-Deoxytetracycline. J. Am. Chem. Soc. 1996, 118, 5304-5305
[15] A.Eschenmoser, C. E. Wintner, Natural product synthesis and vitamin B12. Science 1977, 196, 1410-1420
[16] A.Eschenmoser, Chemical Etiology of Nucleic Acid Structure. Science 1999, 284, 2118-2124
[17] M. Beier, F. Reck, A.Eschenmoser, Chemical Etiology of Nucleic Acid Structure: Comparing Pentopyranosyl-(2' 4') Oligonucleotides with RNA. Science 1999, 283, 699-703
[18] D.H.R.Barton, J. M. Beaton, L.E. Geller, A New Photochemical Reaction. J. Am. Chem. Soc. 1960, 82, 2640-2641
[19] D.H.R.Barton, J. M. Beaton, A Synthesis of Aldosterone Acetate. J. Am. Chem. Soc. 1961, 83, 4083-4089
[20] 易杨华, 李玲, 海洋药物研究展望与对策. 第二军医大学学报 2001, 22(9), 801-802
[21] 张兴德, 刘汉清, 海洋药物研究进展. 南京中医药大学学报 2003, 19(2), 126-128
[22] 王艳, 周培根, 戚晓玉, 海洋生物中毒素的研究进展. 上海水产大学学报2002, 11(3), 283-288
[23] George R. Pettit, Yoshiaki Kamano, Cherry L. Herald, Isolation of dolastatins 10–15 from the marine mollusc dolabella auricularia. Tetrahedron 1993, 49, 9151-9170
[24] George R. Pettit, Sheo Bux Singh, Fiona Hogan, Antineoplastic agents. Part 189. The absolute configuration and synthesis of natural (-)-dolastatin 10. J. Am. Chem. Soc. 1989, 111, 5463-5465
[25] Poncet J., Busquet M., Roux F., Synthesis and Biological Activity of Chimeric Structures Derived from the Cytotoxic Natural Compounds Dolastatin 10 and Dolastatin 15. J. Med. Chem. 1998, 41(9), 1524-1530
[26] George R. Pettit, Yoshiaki Kamano, Claude Dufresne, Isolation and structure of the cytostatic linear depsipeptide dolastatin 15. J. Org. Chem. 1989, 54, 6005-6006
[27] George R. Pettit, Delbert L. Herald, Sheo Bux Singh, Antineoplastic agents. 220. Synthesis of natural (-)-dolastatin 15. J. Am. Chem. Soc. 1991, 113, 6692-6693
[28] George R. Pettit, Yoshiaki Kamano, Cherry L. Herald, Structure of bryostatin. 4. An important antineoplastic constituent of geographically diverse Bugula neritina (Bryozoa). J. Am. Chem. Soc. 1984, 106, 6768-6771
[29] 关美君, 林文翰, 丁源, 海洋药物--二十一世纪中国药学研究的新热点. 中国海洋药物 2001, 79, 1-5
[30] 黄建设, 龙丽娟, 海洋天然产物及其生理活性的研究进展. 海洋通报 2001, 20(4), 83-91
[31] 林厚文, 易杨华, 姚新生, 南中国海总合草苔虫中一个新的抗肿瘤化合物:Bryostatin19. 中国海洋药物 1998, 17(1), 1
[32] Sakai R. Rinehart, K. kishore, Structure-activity relationships of didemnis. J. Med. Chem. 1996, 39(14), 2819
[33] 姚新生, 易杨华, 汤海峰等, 海洋抗肿瘤物质研究概况与展望. 药学服务与研究 2002, 2(1), 7-16
[34] Lindel T., Jensen P. R., Fenical W., Eleutherobin, a New Cytotoxin that Mimics Paclitaxel (Taxol) by Stabilizing Microtubules. J. Am. Chem. Soc. 1997, 119, 8744-8745
[35] Sarath P. Gunasekera, Malika Gunasekera, Ross E. Longley, Discodermolide: a new bioactive polyhydroxylated lactone from the marine sponge Discodermia dissolute. J. Org. Chem. 1990, 55, 4912-4915
[36] Amy E. Wright, Dorilyn A. Forleo, Geewananda P. Gunawardana, Antitumor tetrahydroisoquinoline alkaloids from the colonial ascidian Ecteinascidia turbinate. J. Org. Chem. 1990, 55, 4508-4512
[37] Kenneth L. Rinehart, Tom G. Holt, Nancy L. Fregeau, Ecteinascidins 729, 743, 745, 759A, 759B, and 770: potent antitumor agents from the Caribbean tunicate Ecteinascidia turbinate. J. Org. Chem. 1990, 55, 4512-4515
[38] Gerwick W. H., Proteau P. J., Nagle D. G. , Structure of Curacin A, a Novel Antimitotic, Antiproliferative and Brine Shrimp Toxic Natural Product from the Marine Cyanobacterium Lyngbya majuscula. J. Org. Chem. 1994, 59, 1243-1245
[39] James C Muir, Gerald Pattenden, Tao Ye, A concise total synthesis of (+)-curacin A, a novel cyclopropyl-substituted thiazoline from the cyanobacterium Lyngbya majuscula . Tetrahedron Lett. 1998, 39, 2861-2864
[40] 刘凤云、李赏、周艳荣等,海洋生物毒素的药物开发前景,生物技术通讯2002,13(5),392-394
[41] Satoshi S., Koji M., Kyosuke T., Amino acid sequence of two sea anemone toxins from Anthopjeura fuscovides. Toxicon 1987, 26, 639
[42] 郑星明,王益寿,海洋资源药物开发现状与前景. 上海化工 1999,24(1), 4-5
[43] Michael Z. Hoemann, Konstantinos A. Agrios, Jeffrey Aubé, Total synthesis of curacin A . Tetrahedron Lett. 1996, 37, 953-956
[44] Michael Z. Hoemann, Konstantinos A. Agrios and Jeffrey Aubé, Total synthesis of (+)-curacin A, a marine cytotoxic agent. Tetrahedron 1997, 53, 11087-11098
[45] Wipf P., Xu W., Total Synthesis of the Antimitotic Marine Natural Product (+)-Curacin A. J. Org. Chem. 1996, 61, 6556-6562
[46] Jing-Yu Lai, Jurong Yu, Belew Mekonnen, Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula . Tetrahedron Lett. 1996, 37, 7167-7170
[47] James C. Muir, Gerald Pattenden, Tao Ye, A Concise Total Synthesis of (+)-curacin A, a Novel Cyclopropyl-substituded Thiazoline from the Cyanobacterium Lyngbya majuscula. Tetrahedron Lett. 1998, 39, 2861-2864
[48] Luesch H., Yoshida W. Y., Moore R. E., Isolation, Structure Determination, and Biological Activity of Lyngbyabellin A from the Marine Cyanobacterium Lyngbya majuscula. J. Nat. Prod. 2000, 63, 611-615
[49] Yokokawa F., Sameshima H., Shioiri T., Total synthesis of lyngbyabellin A, a potent cytotoxic metabolite from the marine cyanobacterium Lyngbya majuscula. Tetrahedron 2001, 42, 4171-4174
[50] Xu Z. S., Peng Y. G., Ye T, International Forum On Pharmaceutical Techonology(2002), 70
[51] Clausen K., Thorsen M., Lawesson S. O., Studies on Amino Acids and Peptide-I: Synthesis of N-Benzyloxycarbonylendo-thiodipeptide ester, Tetrahedron 1981, 37, 3635-3639
[52] Wipf P., Fritch P. C., Synthesis of Peptide Thiazolines from β-hydroxythioamides. An Investigation of Racemization in Cyclodehydration Protocals. Tetrahedron Lett. 1994, 35, 5397-5440
[53] Atkins G. M., Burgess E. M. The Reaction of an N-sulfonylamine inner salt. J. Am. Chem. Soc. 1968, 90, 4744-4745
[54] Boden C. D., Pattenden G., Ye T. The Synthesis of Optically active Thiazoline and Thiazole Derived Peptides from N-protected-amino Acids. Synlett. 1995, 417-419
[55] Shalaby M. A., Grote C. W., Rapoport H. Thiopeptide Synthesis: α-Amino Thionoacid Derivatives of Nitrobenzotrizole as Thioacylating Agents. J. Org. Chem. 1996, 61, 9045-9048
[56] Luesch H., Pangilinan R., YoShida W. Y., Pitipeptolides A and B, New Cyclodepsipeptides from the Marine Cyanobacterium Lyngbya majuscula. J.Nat.Prod. 2001,64,304~307
[57] Xu Z. S., Peng Y. G., Ye T, International Forum On Pharmaceutical Techonology (2002), 70
[58] Paul Lloyd-Williams, Fernando albericio, Ernest Giralt. Chemical Approaches to the Synthesis of Peptides and Proteins, New York: CRC Press, 1997, p95-104
[59] Gergory A. Grant, Synthetic Peptides, New York: Oxford University Press, 2002, p93-219
[60] M. Bodanszky, A. Bodanszky, The Practice of Peptide Synthesis, New York: Springer-Verlag, 1984, p7-85, p151-195, p87-150
[61] M. Bodanszky, Principles of Peptide Synthesis, New York: Springer-Verlag, 1984, p59-107, p158-195
[62] Philip J. Kocieński, Protecting Groups, Thieme, 1994, p185-244, p21-87, p118-151
[63] Theodora W. Greene, Protecting Groups in Organic Synthesis, New York: John Wiley & Sons, Inc. 1980, p309-406, p224-277, p10-143
[64] 黄维生, 多肽合成, 北京: 科学出版社, 12-56, p102-p149
[65] Oliver Seitz, New Protecting Group Strategies for the Solid-Phase Synthesis and Modification of Peptides, Oligonucleotides, and Oligosaccharides. Angew. Chem. Int. Ed. 1998, 37(22), 3109-3111
[66] Tohru Fukuyama, Mui Cheung, Chung-Kuang Jow, 2,4-Dinitrobenzenesulfonamides: A Simple and Practical method for the Preparation of a Variety of Secondary Amines and Diamines. Tetrahedron Lett. 1997, 38(33), 5831-5834
[67] James R. Vaughan, Jr. Ruth L. Osato, The Preparation of Peptides Using Mixed Carbonic-Carboxylic Acid Anhydrides. J. Am. Chem. Soc. 1952, 74, 676-678
[68] George Washington Anderson, Joan E. Zimmerman, Francis M. Callahan, Reinvestigation of the mixed carbonic anhydride method of peptide synthesis. J. Am. Chem. Soc. 1967, 89, 5012-5017
[69] So-Yeop Han, Young-Ah Kim, Recent Development of Peptide Coupling Reagents in Organic Synthesis, Tetrahedron 2004, 60, 2447-2467
[70] Jorge I. Jiménez, Paul J. Scheuer, New Lipopeptides from the Caribbean Cyanobacterium Lyngbya majuscula, J. Nat. Prod. 2001, 64, 200-203
[71] Reese M. T., Gulavita N. K., Nakao Y., Kulolide: A Cytotoxic Depsipeptide from a Cephalaspidean Mollusk, Philinopsis speciosa. J. Am. Chem. Soc. 1996, 118, 11081-11084
[72] Nakao Y., Yoshida W. Y., Szabo C. M., More Peptides and Other Diverse Constituents of the Marine Mollusk Philinopsis speciosa. J. Org. Chem. 1998, 63, 3272-3280
[73] George R. Pettit, Jun-Ping Xu, Fiona Hogan, Isolation and Structure of Dolastatin 17. Heterocycles 1998, 47(1), 491-496
[74] Jaime Rodríguez, Rogelio Fernández, Emilio Qui?oá, Onchidin: a cytotoxic depsipeptide with C2 symmetry from a marine mollusk. Tetrahedron Lett. 1994, 35, 9239-9242
[75] Luesch H., Yoshida W. Y., Moore R. E., Apramides A-G, Novel Lipopeptides from the Marine Cyanobacterium Lyngbya majuscula. J. Nat. Prod. 2000, 63, 1106-1112
[76] Stefan Kehraus, Gabriele M. K?nig, Anthony D. Wright, Leucamide A: A New Cytotoxic Heptapeptide from the Australian Sponge Leucetta microraphis, J. Org. Chem. 2002, 67, 4989-4992
[77] David A. Evans, Leester D. Wu, John J. M. Wiener, A General Method for the Synthesis of Enantiomerically Pure β-Substituted, β-Amino Acids through α-Substituted Succinic Acid Derivatives. J. Org. Chem. 1999, 64, 6411-6417
[78] Peter Wipf, Yuntae Kim, Paul C. Fritch. Total Synthesis and Structure Assignment of the Antitumor Antibiotic Aranorosin. J. Org. Chem. 1993, 58, 7195-1203
[79] Richard E. Taylor, Yue Chen, Total Synthesis of Epothilones B and D. Organic Letters 2001, 3(14), 2221-2224
[80] Carl P. Decicco, David J. Nelson, Ronald L. Corbett, Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of a-Trifluoromet hanesulfonat e Substituted Esters. J. Org. Chem. 1996, 60, 4782-4785
[81] Marco Lerm, Hans-Joachim Gais, Kejun Cheng, Asymmetric Synthesis of the Highly Potent Anti-Metastatic Prostacyclin Analogue Cicaprost and Its Isomer Isocicaprost. J. Am. Chem. Soc. 2003, 125, 9653-9667
[82] D. A. Evans, M. D. Ennis, D. J. Mathre, Asymmetric Alkylation Reactions of Chiral Imide Enolates. A Practical Approach to the Enantioselective Synthesis of a-Substituted Carboxylic Acid Derivatives. J. Am. Chem. Soc. 1982, 104, 1737-1739
[83] Michael G. Organ, Yaroslav V. Bilokin, Svetoslav Bratovanov, Approach toward the Total Synthesis of Orevactaene. 2. Convergent and Stereoselective Synthesis of the C18-C31 Domain of Orevactaene. Evidence for the Relative Configuration of the Side Chain, J. Org. Chem. 2002, 67, 5176-5183
[84] Jennifer L. Belelie, J. Michael Chong, Stereoselective Reactions of Acyclic Allylic Phosphates with Organocopper Reagents, J. Org. Chem. 2001, 66, 5552-5555
[85] Victor Garcia-Ruiz, Simon Woodward, On the absolute stereochemistry of (-)-4-alkylnonan-2-ones. Tetrahedron: Asymmetry 2002, 13, 2177–2180
[86] David A. Evans, Mark T. Bilodeau, Todd C. Somers, Enantioselective Michael Reactions. Diastereoselective Reactions of Chlorotitanium Enolates of Chiral N-Acyloxazolidinones with Representative Electrophilic Olefins. J. Org. Chem. 1991, 56, 5750-5752
[87] Khuong Mai, Ghanshyam Patil, Alkylsiyl Cyanides as Silyating Reagents. J. Org. Chem. 1986, 51, 3545-3548
[88] Guy Solladié, Francoise Colobert Colobert, Chakib Kala?, Stereoselective Synthesis of All-trans Methyl Substiuted Polyenes by Reductive Elimination and Application to the Synthesis of All-trans 3-Methyl-nona-2,4,6-trienol. Tetrahedron Lett. 2000, 41, 4197-4200
[89] Gary A. Molander, Jan Antoinette C. Romero, Christopher P. Corrette, Hydrosilylation of Alkynlsilanes Utilizing Organlanthanide and Group 3 Metallocene Complexes. Journal of Oraganmetallic Chemistry 2002, 647, 225-235
[90] Ei-ichi Negishi, Larry D. Boardman, Hiroyuki Sawada, Novel Cyclialkylation Reactions of (ω-Halo-1-alkenyl)metal Derivatives. Synthetic Scope and Methanism. J. Am. Chem. Soc. 1988, 110, 5383-5396
[91] Scott E. Schaus, Jonas Branalt, Eric N. Jacobsen, Total Synthesis of Muconin by Efficient Assembly of Chiral Building Blocks. J. Org. Chem. 1998, 63, 4876-4877
[92] Ulrich Berlage, Jürgen Schmidt, Ulrike Peters, A formal total synthesis of (±)-strigol. Tetrahedron Lett. 1987, 28, 3091-3094
[93] E. J. Corey, Ryu Nagata, Synthesis of three new dehydroarachidonic acid derivatives and their oxidation by soybean lipoxygenase. Tetrahedron Lett. 1987, 28, 5391-5394
[94] Carl P. Decicco, Paul Grover, Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A. J. Org. Chem. 1996, 61, 3534-3541
[95] Stacie S. Canan Koch, A. Richard Chamberlin, Enantioselective Preparation of 8-Alkyl-y-butyrolactones from Functionalized Ketene Dithioacetals, J. Org. Chem. 1993, 58, 2725-2737
[96] Serge David, Annie Thieffry, Conversion of One Hydroxy Group in a Diol to a Phenyl Ether with Triphenylbismuth Diacetate, a New Glycol Reaction Showing Strong Axial Preference in Six-Membered Rings. J. Org. Chem. 1983, 48, 441-447
[97] Patrick G. McDougal, Joseph G. Rico, Young-Im Oh, A Convenient Procedure for the Monosilylation of Symmetric 1,n –Diols. J. Org. Chem. 1986, 51, 3388-3390
[98] Kanji Omura, Daniel Swern, Oxidation of Alcohols by “Activated” Dimethyl Sulfoxide. A Preparative, Steric and Mechanistic Study. Tetrahedron 1978, 34, 1651-1660
[99] James A. Marshall, Marc W. Andersen, Synthesis of 12-, 14-, and 16-Membered Propargylic Alcohols through Lewis Acid-Promoted Ene Cyclization. J. Org. Chem. 1993, 58, 3912-3918
[100] Steven Wolff, Bhaskar Rao Venepalli, Clifford F. George, Some Thermal and Photochemical Reactions of [ 4.4.4.5 ] Fenestranes. J. Am. Chem. Soc. 1988, 110, 6785-6790
[101] B. C. Hamper, α-Acetylenic Esters From α-Acylmethylenephosphoranes: Ethyl 4,4,4-Trifluorotetrolate, Organic Syntheses CV 9, 436
[102] Robert W. Lang, Hans-Jürgen Hansen, α-Allenic Esters from α-Phosphoranylidene Esters and Acid Chlorides: Ethyl 2,3-Pentadienoate. Organic Syntheses CV 7, 232
[103] Andrew D. Abell, Kathryn B. Morris, J. Christopher Litten, Synthesis and Deprotection of [ 1-( Et hoxycarbony1)-4-[ (diphenylmet hoxy )carbonyl]-1-met hyl-2-oxobutyl]-triphenylphosphonium Chloride: A Key Intermediate in the Wittig Reaction between a Cyclic Anhydride and a Stabilized Ylide. J. Org. Chem. 1990, 55, 5217-5221
[104] Gregory R. Cook, Lars G. Beholz, John R. Stille, Construction of Hydroxylated Alkaloids (f )-Mannonolactam, (f )-Deoxymannojirimycin, and (f ) -Prosopinine through aza-Annulation. J. Org. Chem. 1994, 59, 3575-3584
[105] Wolfgang Barth, Leo A. Paquette, Synthesis of a representative cis/trans pair of 4,5-disubstituted cyclopentenyllithium reagents. J. Org. Chem. 1985, 50, 2438-2443
[106] Franciszek Kazmierczak, Paul Helquist, Synthesis of the branched nine-carbon unit of the type A streptogramins and other antibiotics. J. Org. Chem. 1989, 54, 3988-3992
[107] Lanchi Vo, James Ciula, Owen W. Gooding, Chemical Development on the Chiral Auxiliary (S)-4-(Phenylmethyl)-2-oxazolidinone Utilizing Automated Synthesis and DoE. Organic Process Research & Development 2003, 7, 514-520
[108] David A. Evans, Thomas C. B&ton, Jon A. Ellman, Contrasteric Carboximide Hydroolysis with Lithium Hydroperoxide. Tetrahedron Lett. 1987, 28(49), 6141-6144
[109] D. A. Evans, J. Bartroli, T. L. Shih, Enantioselective Aldol Condensations. 2. Erythro-Selective Chiral Aldol Condensations via Boron Enolates. J. Am. Chem. Soc. 1981, 103, 2127-2129
[110] Th. J. de Boer, H. J. Backer, Diazomethane. Organic Syntheses CV 4, 250
[111] Th. J. de Boer, H. J. Backer, p-Tolylsulfonylmethylnitrosamide. Organic Syntheses CV 4, 943
[112] David R. Williams, David L. Brown, John W. Benbow, Studies of Stemona Alkaloids. Total Synthesis of (+)-Croomine. J. Am. Chem. Soc. 1989, 111, 1923-1925
[113] Stephan Muller, Bemd Liepold, Gerald J. Roth, An Improved One-pot Procedure for the Synthesis of Alkynes from Aldehydes. Synlett. 1996, 521-522
[114] K. C. Nicolaou, F. Murphy, S. Barluenga, Total Synthesis of the Novel Immunosuppressant Sanglifehrin A. J. Am. Chem. Soc. 2000, 122, 3830-3838
[115] William R. F. Goundry, Jack E. Baldwin, Victor Lee, Total synthesis of cytotoxic sponge alkaloids hachijodines F and G. Tetrahedron 2003, 59, 1719–1729
[116] Miyuki Ishizaki, Kazuhiko Iwahara, Yuka Niimi, Investigation of the synthesis of angular tricyclic compounds by intramolecular Pauson±Khand reaction of exo-and endo-cyclic enynes. Tetrahedron 2001, 57, 2729-2738;Yoshitaka Matsushima, Hiroaki Itoh, Takuya Nakayama, Enantioselective total synthesis of vicenistatin, a novel 20-membered macrocyclic lactam antitumor antibiotic. J. Chem. Soc., Perkin Trans. 2002, 1, 949–958
[117] Harris, Christopher, John, Beta-Ketophosphonates, US, WO03027129, 20030403
[118] Tohru Fukuyama, Chung-kuang Jow, Mui Cheung, 2-and 4-Nitrobenzenesulfonamides: Exceptionally Versatile Means for Preparation of Secondary Amines and Protection of Amines. Tetrahedron Lett. 1995, 36(36), 6373-6374
[119] Edwin Vedejs, Chutima Kongkittingam, Solution-Phase Synthesis of a Hindered N-Methylated Tetrapeptide Using Bts-Protected Amino Acid Chlorides: Efficient Coupling and Methylation Steps Allow Purification by Extraction. J. Org. Chem. 2000, 65, 2309-2318
[120] W. Russell Bowman, Daniel R. Coghlan, A Facile Method for the N-Alkylation of α-Amino Esters. Tetrahedron 1997, 53(46), 15787-15798
[121] Engel K-H., Lipase-catalyzed enantioselective esterification of 2-methylalkanoic acids. Tetrahedron: Asymmetry 1991, 2, 165-168
[122] Berglund P., Holmquist M., Hedenstr?m E., 2-Methylalkanoic acids resolved by esterification catalysed by lipase from Candida rugosa: Alcohol chain length and enantioselectivity. Tetrahedron: Asymmetry 1993, 4, 1869-1878
[123] Hu J., Miller M. J., Total Synthesis of a Mycobactin S, a Siderophore and Growth Promoter of Mycobacterium Smegmatis, and Determination of its Growth Inhibitory Activity against Mycobacterium tuberculosis. J. Am. Chem. Soc. 1997, 119, 3462-3468
[124] Prakash Raman, Suzanne S. Stokes, Yvonne M. Angell, Methods to Circumvent a Difficult Coupling in the Solid-Phase Synthesis of Cyclosporine Analogues. J. Org. Chem. 1998, 63, 5734-5735
[125] Injae Shin, Kisoo Park, Solution-Phase Synthesis of Aminooxy Peptoids in the C to N and N to C Directions. Organic Lett. 2002, 4(6), 869-872
[126] Jaume Farràs, Xavier Ginesta, Pedro Romea, β3-Amino acids by nucleophilic ring-opening of N-nosyl aziridines. Tetrahedron 2001, 57, 7665-7674
[127] Stephen C. Miller, Thomas S. Scanlan, oNBS-SPPS: A New Method for Solid-Phase Peptide Synthesis. J. Am. Chem. Soc. 1998, 120, 2690-2691
[128] Juan Cabre, Antonio Luis Palomo, New Experimental Strategies in Amide Synthesis using N,N-Bis[2-oxo-3-oxazolidinyl]phosphorodiamidic Chloride. Synthesis. 1984, 413-417
[129] Yvonne M. Angell, Carlos Garcia-Echeverria, aniel H. Rich, Comparative Studies of the Coupling of N-Methylated, Sterically Hindered mino Acids During Solid-Phase Peptide Synthesis. Tetrahedron Lett. 1994, 35(33), 5981-5984
[130] Rdger D. Tung, Daniel H. Rich, Bis(2-oxo-3-oxazolidinyl)phosphinic Chloride as a Coupling Reagent for N-Alkyl Amino Acids. J. Am. Chem. Soc. 1985, 107, 4342-4343
[131] J. Diago-Meseguer, A. L. Palomo, A New Reagent for Activating Carboxyl Groups;Preparation and Reactions of N,N-Bis[2-oxo-3-oxazolidinyl] phosphorodiamidic Chloride. Synthesis. 1980, 547-551
[132] Estelle Dumez, John S. Snaith, Richard F. W. Jackson, Synthesis of Marcocylic, Protential Protease Inhibitiors Using a Generic Scaffold, J. Org. Chem. 2002, 67, 4882-4892
[133] Luiz C. Dias, Andrea A. Ferreira, Gaspar Diaz, Short Total Synthesis of Aspartyl Protease Inhibitors L-685,434, L-682,679 and L-685,458, Synlett. 2002, (11), 1845-1849
[134] Rodney L. Parsons, Clayton H. Heathcock, Total Synthesis of Mirabazole B, Tetrahedron Lett. 1994, 35(9), 1383-1384
[135] Alam Dal Pozzo, Laura Muzi, Maurizio, etc., Synthesis of RGD Analogues Containing α-Tfm-Arginine as Potential Fibrinogen Receptor Antagonists, Tetrahedron 1998, 54, 6019-6028
[136] Bryan C. N. M. Jones, John C. Drach, Jiri Zemlicka, etc., (+-)-N9-(2-(Hydroxymethyl)spiro[3.3]hept-6-yl)adenine. The First Biologically Active Saturated Analog of Adenallene with Axial Dissymmetry. J. Org. Chem. 1995, 60, 6277-6280
[137] Azzouz BenCheikh, Leslie E. Craine, Jiri Zemlicka, etc., Synthesis of Racemic 6'β-Hydroxyaristeromycin. A Hydroxycarbocyclic Analogue of Adenosine, J. Org. Chem. 1988, 53(5), 929~936
[138] M. Ashraf Shalaby, Christopher W. Grote, Henry Rapoport, Thiopeptide Synthesis. r-Amino Thionoacid Derivatives of Nitrobenzotriazole as Thioacylating Agents. J. Org. Chem. 1996, 61, 9045-9048
[139] Paul J. Stevenson, Alan B. Treacy, Mark Nieuwenhuyzen, Preparation of Dess–Martin periodinane—the role of themorphology of 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide precursor. J. Chem. Soc., Perkin Trans. 2 1997, 589-591
[140] Stephanie D. Meyer, Stuart L. Schreiber, Acceleration of the Dess-Martin Oxidation by Water. J. Org. Chem. 1994, 59, 7549-7552
[141] Robert E. Ireland, Longbin Liu, An Improved Procedure for the Preparation of the Dess-Martin Periodinane, J. Org. Chem. 1993, 58, 2899
[142] Edward M. Burgess, Harold R. Penton, Conversion of primary Alcohols to urethanes via the inner salt of methyl(carboxysulfamoyl)triethylammonium hydroxide:methyl n-hexylcarbamate. Organic Syntheses CV 6, 788
[143] Peter Wipf, Srikanth Venkatraman, An Improved Protocol for Azole Synthesis with PEG-Supported Burgess Reagent. Tetrahedron Lett. 1996, 37(27), 4659-4662
[144] M. Ashraf Shalaby, enry Rapoport, A General and Efficient Route to Thionoesters via Thionoacyl Nitrobenzotriazoles. J. Org. Chem. 1999, 64, 1065-1070