新型含磷多肽缩合剂的研究与应用
摘要
本论文主要内容是新型、高效含磷多肽缩合剂的设计、合成及其应用方面的研究。基于对现有多肽缩合剂方面的文献报道的研究,发现:(1)通过形成羧酸-磷酸,羧酸-膦酸混合酸酐中间体的缩合剂或缩合方法,混酐在氨解的时候氨基(NH_(2-))氮原子只进攻羧酸的C=O部分,而不进攻P=O,这种区域选择性能够大大提高反应的产率,同时有效降低产物的消旋率,非常适合多肽合成的要求;(2)脲正离子类型的缩合剂,无论是反应活性,还是在产物的收率和光学纯度方面,都普遍优于其它类型的缩合剂,体现了很强的优越性。综合以上分析,我们设计了一类新型的含磷多肽缩合剂,它的分子中同时含有这两种类型缩合剂的结构((?)R~1,R~2=alkyl,alkyl-oxy,aryl,F,Cl,Br;A=F,Cl,Br,OBt,OAt,OOBt)。
这类缩合剂中最简单的一种是((?))。它不需要预先制备,POCl_3和4-N,N-二甲基吡啶(DMAP)在溶液中可以“现场”生成。Cbz-Phe-OH和H_2N-Leu-OMe-HCl的缩合被用作模型反应,来优化反应所需的最佳条件:选用CH_2Cl_2作为溶剂,三乙胺作为碱,0.3当量的DMAP作为催化剂,在冰水浴的条件下进行反应0.5-1h左右最为合适。用此种方法在最优反应条件下合成了16种具有不同侧链的保护二肽,产率都在90%以上,而其消旋率≤2.1%(手性OD柱)。
这种类型的缩合剂不仅可以用于酰胺键的形成而且可以用于酯键的形成。我们用这种缩合剂合成了20种具有不同官能团的酯,产率高(95%左右)而且反应物侧链含有的双键、三键等官能团不受影响;一些用常规方法很难实现的长链酸(C_(18))、长链醇(C_(18))的缩合,用该种方法2h即可获得80%以上的产率;另外,此类缩合剂己被实验验证了能够有效地应用于天然抗肿瘤药物BFA的酯化结构改造反应中,反应中3h即可获得82%的产率。
最后,通过合理的方案设计,论文中用~(31)PNMR跟踪的方法初步证明了此种缩合剂的作用机理。DMAP在整个反应过程中起到两次催化作用;第一次,与POCl_3反应形成复合物((?));第二次,与混酐反应形成中间体((?)),POCl_3则于反应后以最终副产物Cl_2PO_2~-的形式存在。
This dissertation was focused on the design and synthesis of novel peptide coupling reagents, as well as their applications in peptide synthesis. Based upon our studies about peptide coupling reagent reported in litreture, it was found that: (1) The novel reagents would form phosphinic carboxylic mixed anhydrides, which undergoes aminolysis by attack at the carbonyl group. And the regiospecificity is dependent upon the nature of the nucleophile, which compatible with the requirements of peptide synthesis; (2) The uronium salts were proved to be superior to others in both reactivity and racemization. Herein, we designed a new type of efficient coupling reagents, with the molecular structures contained not only phosphinic but also uroniumsalts((?)R~1,R~2=alkyl,alkyl-oxy,aryl,F,Cl,Br;A=F,Cl , Br, OBt, OAt,OOBt).
The most simpliest one among the new type of coupling reagents is(?), which can be produced in situ by POCl_3 reacting with DMAP insolution. As a model system, the coupling of Cbz-Phe-OH and K_2N-Leu-OMeHCl was carried out. After studying the reaction mechanism, POCl_3 was chosen as the coupling reagent for the peptide synthesis. Thus, 16 bioactive peptides were synthesized under the same conditions, uneventfully afforded dipeptides in high yield. Specific rotations of dipeptides were consistent with those in litreture. HPLC [CHIRAL-CEL(OD)] analysis of dipeptides further confirmed their diastereomeric purity.
It could be used not only for the synthesis of amides, but also for esters synthesis. 20 esters with all sorts of function groups were synthsized in high yield, even for the long chain carbolic acids and long chain alcohols. And it has been used for the modification of the molecular structure of BFA, which possesses a divers array of biological activities including antiviral,fungal,ematocidal and antitumor effects.
Finally, the mechanism for phosphinic carboxyiic mixed anhydrides mediatedcoupling reaction was also investigated by ~(31)P NMR.lt is indicated that DMAP act ascatalyst: First, it was reacted with POCl_3 to give (?), then it was reacted withphosphinic carboxyiic mixed anhydrides to give
这类缩合剂中最简单的一种是((?))。它不需要预先制备,POCl_3和4-N,N-二甲基吡啶(DMAP)在溶液中可以“现场”生成。Cbz-Phe-OH和H_2N-Leu-OMe-HCl的缩合被用作模型反应,来优化反应所需的最佳条件:选用CH_2Cl_2作为溶剂,三乙胺作为碱,0.3当量的DMAP作为催化剂,在冰水浴的条件下进行反应0.5-1h左右最为合适。用此种方法在最优反应条件下合成了16种具有不同侧链的保护二肽,产率都在90%以上,而其消旋率≤2.1%(手性OD柱)。
这种类型的缩合剂不仅可以用于酰胺键的形成而且可以用于酯键的形成。我们用这种缩合剂合成了20种具有不同官能团的酯,产率高(95%左右)而且反应物侧链含有的双键、三键等官能团不受影响;一些用常规方法很难实现的长链酸(C_(18))、长链醇(C_(18))的缩合,用该种方法2h即可获得80%以上的产率;另外,此类缩合剂己被实验验证了能够有效地应用于天然抗肿瘤药物BFA的酯化结构改造反应中,反应中3h即可获得82%的产率。
最后,通过合理的方案设计,论文中用~(31)PNMR跟踪的方法初步证明了此种缩合剂的作用机理。DMAP在整个反应过程中起到两次催化作用;第一次,与POCl_3反应形成复合物((?));第二次,与混酐反应形成中间体((?)),POCl_3则于反应后以最终副产物Cl_2PO_2~-的形式存在。
This dissertation was focused on the design and synthesis of novel peptide coupling reagents, as well as their applications in peptide synthesis. Based upon our studies about peptide coupling reagent reported in litreture, it was found that: (1) The novel reagents would form phosphinic carboxylic mixed anhydrides, which undergoes aminolysis by attack at the carbonyl group. And the regiospecificity is dependent upon the nature of the nucleophile, which compatible with the requirements of peptide synthesis; (2) The uronium salts were proved to be superior to others in both reactivity and racemization. Herein, we designed a new type of efficient coupling reagents, with the molecular structures contained not only phosphinic but also uroniumsalts((?)R~1,R~2=alkyl,alkyl-oxy,aryl,F,Cl,Br;A=F,Cl , Br, OBt, OAt,OOBt).
The most simpliest one among the new type of coupling reagents is(?), which can be produced in situ by POCl_3 reacting with DMAP insolution. As a model system, the coupling of Cbz-Phe-OH and K_2N-Leu-OMeHCl was carried out. After studying the reaction mechanism, POCl_3 was chosen as the coupling reagent for the peptide synthesis. Thus, 16 bioactive peptides were synthesized under the same conditions, uneventfully afforded dipeptides in high yield. Specific rotations of dipeptides were consistent with those in litreture. HPLC [CHIRAL-CEL(OD)] analysis of dipeptides further confirmed their diastereomeric purity.
It could be used not only for the synthesis of amides, but also for esters synthesis. 20 esters with all sorts of function groups were synthsized in high yield, even for the long chain carbolic acids and long chain alcohols. And it has been used for the modification of the molecular structure of BFA, which possesses a divers array of biological activities including antiviral,fungal,ematocidal and antitumor effects.
Finally, the mechanism for phosphinic carboxyiic mixed anhydrides mediatedcoupling reaction was also investigated by ~(31)P NMR.lt is indicated that DMAP act ascatalyst: First, it was reacted with POCl_3 to give (?), then it was reacted withphosphinic carboxyiic mixed anhydrides to give
引文
[1] [德]N．休厄德．；H．D．贾库布克 著；刘克良，何军林等译．肽：化学与生物学．北京：科学出版社，2005．
[2] Memfield, R. B. J. A. Chem. Soc. 1963,55,2149.
[3] 黄惟德，陈常庆．多肽合成．北京：科学出版社，1985．
[4] (a) Mckay, S. C; Albertson, N. F. J. Am. Chem. Soc. 1957, 79, 4686. (b) Anderson, G W.; Mcgregor, A. G J. Am. Chem. Soc. 1957, 79, 6180.
[5] (a) Carpino, L. A. Acc. Chem. Res. 1987,20,401. (b) Carpino, L. A.; Han, G Y. J. Am. Chem.Soc. 1970, 92, 5748.
[6] Carpino, L. A.; Chao, H. G; Beyermann, M; Bienert, M. J. Org. Chem. 1991, 56,2635.
[7] Carpino, L. A.; Sadat-Aalee, D.; Chao, H. G; Deselms, R. J. Am. Chem. Soc. 1990,112, 9651.
[8] Denkewalter, R. G; Schwarm, H.; Strachan, R. G J. Am. Chem. Soc. 1966,88,3163.
[9] Hirschamann, R.J. Org. Chem. 1967,32, 3415.
[10] (a) Auvin-Guette, C; Frerot, E.; Coste, J.; Rebuffat, S.; Jouin, P.; Bodo, B. Tetrahedron Lett. 1993, 34, 2481. (b) Swain, P. A.; Anderson, B. L.; Goodman, M.; Fuller, W. D. Pept. Res. 1993, 6,147.
[11] (a) Anderson, G W.; Zimmerman, J. F.; Callaham, F. M. J. Am. Chem. Soc. 1966,88, 1334. (b) Anderson, G W.; Zimmerman, J. F.; Callaham, F. M. J. Am. Chem. Soc. 1967,89,5012.
[12] Kurz, H.Angew. Chem., Int. Ed. 1978,17, 67.
[13] Gorecka, A.; Leblawy, M.; Zabrocki, J.; Zwierzak, A. Synthesis 1978,474.
[14] (a) Ramage, R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G W.; Moore, G A. J. Chem. Soc, Perkin Trans. 1.1985,461. (b) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. J. Chem. Soc, Perkin Trans. 1.1985,1617.
[15] Manhas, M. S. Syn. Commun. 1976, 6,435.
[16] Jockson, A. G; Kenner, G W.; Moore, G A.; Ramage, R.; Thorpe, W. D. Tetrahedron Lett. 1976,17, 3627.
[17] Ramage, R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G W.; Moore, G A. J. Chem. Soc, Perkin Trans. 1. 1985,461.
[18] Galpin, I. J.; Robinson, A. E. Tetrahedron Lett. 1984,25, 627.
[19] Galpin, I. J.; Mohammed, A. K.; Patel, A. Tetrahedron. 1988, 44,1685.
[20] (a) Young, R.W.; Wood, K. H.; Joyce, R. J.; Anderson, G W. J. Am. Chem. Soc. 1956, 78, 2126. (b)Crofts, P.C.; Markes, J. H. H.; Rydon, H. N. J. Chem. Soc. 1959,3610.
[21] (a) Tung, R. D.; Rich, D. H. J. Am. Chem. Soc. 1985, 707,4342. (b) Tung, R. D.; Dhaon, M. K.; Rich, D. H. J. Org. Chem. 1986, 57, 3350. (c) Van Der Auwera, C; Van Damme, S.; Anteunis, M. J. O. Int. J. Peptid Protein Res. 1987,29,464.
[22] Van Der Auwera, C; Anteunis, M.J.O. Int J. Peptid Protein Res. 1987,29, 574.
[23] (a) Kisfaludy, L.; Low, M.; Nyeki, O.; Szirtes, R.; Schon, I. Justus Liebigs Ann.Chem. 1973, 1421. (b) Kovacs, J.; Kisfaludy, L.; Ceprini, M. Q. J. Am. Chem. Soc. 1967, 89, 183. (c) Kisfaludy, L. J. Org. Chem. 1970,35, 3565. (d) Kisfaludy, L.; Schon, I.; Szirtes, T; Nyeki, O.; Low, M. Tetrahedron Lett.1914,15,1785. (e) Kisfaludy, L.; Schon, I. Synthesis 1983,325.
[24] Kovacs, J.; Mayers, G L.; Johnson, K. H.; Cover, R. E.; Ghatak, U. R. Chem.Commun. 1970, 53.
[25] (a) Atherton, E.; Cameron, L. R.; Sheppard, R. C. Tetrahedron. 1988, 44, 843. (b) Atherton, E.; Sheppard, R. C. Chem.Commun. 1985, 165. (c) Meldal, M.; Jensen, K. J.; Chem.Commun. 1990,483.
[26] Nefkens, G H. L.; Tesser, G I. J. Am. Chem. Soc. 1961,83, 1263.
[27] (a) Anderson, G W.; Zimmernan, J. E.; Callahan, F. M. J. Am. Chem. Soc. 1963,85, 3039. (b) Anderson, G W.; Zimmernan, J. E.; Callahan, F. M. J. Am. Chem. Soc. 1964, 86, 1839.
[28] (a) Konig, W.; Geiger, R. Chem.Ber. 1970,103, 2024. (b) Konig, W.; Geiger, R. Chem. Ber. 1970,103, 2034.
[29] (a) Atherton, E.; Cameron, L.; Meldal, M.; Sheppard, R. C. Chem.Commun. 1986, 1763. (b) Atherton, E.; Holder, J. L.; Meldal, M.; Sheppard, R. C; Valerio, R. M. J. Chem. Soc, Perkin Trans. 1. 1988, 2887. (c) Breipohl, G; Knolle, J.; Stuber, W. Int. J. Peptide Protein Res. 1989, 34, 262.
[30] Friedrich, R.; Sheppard, R. C; Steglich, W. Chem.Commun. 1987, 1870.
[1] Sheehan, J. C; Hess, G P. J. Am. Chem. Soc. 1955, 77, 1067.
[2] Sarantakis, D.; Teichman, J.; Lien, E. L.; Fenichel, R. Biochem. Biophys. Res. Commun. 1976, 73, 336.
[3] Shechan, J. C; Cruichshank, P. A.; Boshart, G L. J. Org. Chem. 1961,26,2525.
[4] Gibson, F. S.; Park, M. S.; Rapoport, H. J. Org. Chem. 1994, 59, 7503.
[5] Wunsch, E.; Drees, E. Chem, Ber. 1966,99, 110.
[6] Konig, W.; Geiger, R, Chem, Ber. 1970,103,788.
[7] Carpino, L. A. J. Am. Chem. Soc. 1993,115,4397.
[8] Konig, W.; Geiger, R. Chem.Ber.1910,103,2024.
[9] (a) Khorana, H. G; Todd, A. R. J. Chem. Soc. 1953, 2257. (b) Smith, M.; Moffatt, J. G; Khorana, H. G J. Am. Chem. Soc. 1958,80, 6204.
[10] (a) Rebek, J.; Feitler, D. J. Am. Chem. Soc. 1974, 96, 1606. (b) Detar, D. E.; Silverstein, R. J. Am. Chem. Soc. 1966,88,1013.
[11] Hudson, D. J. Org. Chem. 1988, 53, 617.
[12] Weygand, F. Angew.Chem.1963,75 282.
[13] Gawne, G; Kenner, G; Sheppard, R. C. J. Am. Chem. Soc. 1969, 91, 5669.
[14] (a) Yamada, S.; Takeuchi, Y. Tetrahedron Lett.1971, 12, 3595. (b) Wieland, T.; Seeliger, A. Chem, Ber. 1971,104, 3992.
[15] Bates, A. J.; Galpin, I. J.; Hallett, A.; Hudson, D.; Kenner, G. W.; Ramage, R.; Sheppard, R. C. Helv. Chim. Acta. 1975, 58, 688.
[16] Castro, B.; Dormoy, J. R.; Evin, G; Selve, C. Tetrahedron Lett.1975,16, 1219.
[17] (a) Castro, B.; Dormoy, J. R.; Evin, G; Selve, C. J. Chem. Res.(S) 1977, 182. (b) Felix, A. M.; Wang, C. T.; Heimer, E. P.; Fournier, A. Int. J. Pept. Protein Res. 1988, 31, 231. (c) Forest, M.; Fournier, A. Int J .Pept .Protein Res. 1990, 35, 89. (d) Jarrett, J. T.; Lansbury, P. T. Tetrahedron Lett. 1990, 31,4561.
[18] (a) Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett.1990, 31, 205. (b) Hoeg-Jensen, T.; Havsteen, J. M.; Olsen, C. E.; Holm, A. Tetrahedron Lett.1991, 32, 7617.
[19] Campagne, J. M.; Coste, J.; Jouin, P. J. Org. Chem. 1995, 60,5214.
[20] (a) Kim, M. H.; Patel, D. V. Tetrahedron Lett. 1994, 35, 5603. (b) Coste, J.; Campagne, J. M. Tetrahedron Lett. 1995,36,4253.
[21] Coste, J.; Frerot, E.; Jouin, P.; Castro, B. Tetrahedron Lett. 1991,32,1967.
[22] Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. Chem.Commun. 1994,201.
[23] Alsina, J.; Giralt, E.; Albericio, F. Tetrahedron Lett.1996,37,4195.
[24] Coste, J.; Dufour, M. N.; Pantaloni, A.; Castro, B. Tetrahedron Lett.1990,31,669.
[25] Coste, J.; Frerot, E.; Jouin, P. J. Org. Chem. 1994,59,2437.
[26] Frerot, E.; Coste, J.; Pantaloni, A.; Dufour, M. N.; Jouin,P. Tetrahedron.1991,47,259.
[27] (a) Albericio, F.; Cases, M.; Alsina, J.; Triolo, S. A.; Carpino, L. A.; Kates, S. A. Tetrahedron Lett. 1991,38,4853. (b) Han, Y. X.; Albericio, F.; Barany, G J. Org. Chem. 1997, 62,4307. (c) Jou, G; Gonzalez, I.; Albericio, F.; Lloyd-Williams, P.; Giralt, E. J. Org. Chem. 1997, 62, 354. (d) Marsh, I. R.; Bradley, M.; Teague, S. J. Org. Chem. 1997, 62,6199.
[28] Frerot, E.; Coste, J.; Poncet, J.; Jouin, P. Tetrahedron Lett.1992,33,2815.
[29] (a) Dourtoglou, V.; Ziegler, J. C; Gross, B.Tetrahedron Lett.1978, 19, 1269. (b) Dourtoglou, V.; Gross, B.; Lambropoulou, V; Ziodrou, C. Synthesis. 1984, 572.
[30] Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, Tetrahedron Lett.1989,30,1927.
[31] (a) Chen, S.Q.; Xu, J.C. Tetrahedron Lett. 1992, 33, 647. (b) Coste, J.; Frerot, E.; Jouin, P. Tetrahedron Lett. 1991,32, 1967.
[32] Kiso, Y.; Fujiwara, Y; Kimura, T.; Nishitani, A.; Akaji, K. Int. J. Pept. Protein Res. 1992, 40, 308.
[33] (a) Carpino, L. A.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 1994, 35, 2279. (b) Humphrey, J. M.; Aggen, J. B.; Chamberlin, A.R. J. Am. Chem. Soc. 1996, 118, 11759. (c) Wen, J. J.; Spatola, A. F.J.Pept. Res. 1997,49,3.
[34] Ehrlich, A.; Rothemund, S.; Brudel, M.; Beyermann, M.; Carpino, L. A.; Bienert, M. Tetrahedron Lett. 1993,34,4781.
[35] Albericio, F.; Bofill, J. M.; El-Faham, A.; Kates, S. A. J. Org. Chem. 1998, 63, 9678.
[36] Carpino, L. A.; El-Faham, A. J. Org. Chem. 1995, 60, 3561.
[37] Habermann, J.; Kunz, H.; Tetrahedron Lett. 1998,39,265.
[38] Klose, J.; El-Faham, A.; Kenklein, P.; Carpino, L.A.; Bienert, M.; Tetrahedron Lett. 1999,40, 2045.
[39] Story, S. C; Aldrich, J. V. Int. J. Pept. Protein Res. 1994, 43, 292.
[40] Anteunis, M. J. O.; Sharma,N. K. Bull. Soc. Chim. Belg. 1988, 97,281.
[41] (a) Carpino, L. A.; El-Faham, A. J. Am. Chem. Soc. 1995,117, 5401. (b) Vojkovsky, T.; Drake, B. Org.Prep.Proced,Int. 1997,29,497.
[42] El-Faham, A. Chem. Lett. 1998, 671.
[43] Akaji, K.; Kuriyama, N.; Kiso.Y.; Tetrahedron Lett. 1994,35,3315.
[44] (a) Akaji, K.; Hayashi, Y.; Kiso, Y.; Kuriyama, N. J. Org. Chem. 1999, 64,405. (b) Akaji, K.; Tamai, Y; Kiso, Y. Tetrahedron Lett. 1997,53, 567.
[45] (a) Van der Auwera, C; Anteunis, M. J. O. Int. J. Pept. Protein Res. 1987, 29, 574. (b) Van der Auwera, C; Anteunis, M. J. O. Bull. Soc. Chim. Belg. 1986,95,203.
[46] Chen, S. Q.; Xu, J. C. Chin. J. Chem. 1995,13,175.
[47] Chen, S. Q.; Xu, J. C. Tetrahedron Lett. 1991, 32,6711.
[48] (a) Li, H.; Jiang, X.; Ye, Y H.; Fan, C. X.; Romoff, T.; Goodman, M. Org. Lett. 1999,1, 91. (b) Fan, C. X.; Hao, X. L.; Ye, Y. H. Synth, Commun. 1996, 26, 1455.
[49] Belleau, B.; Malek, G J. Am. Chem. Soc. 1968,90,1651.
[50] (a) Tung, R. D.; Dhaon, M. K.; Rich, D. H. J. Org. Chem. 1986, 57, 3350. (b) Colucci, W.J.; Tung, R. D.; Petri, J. A.; Rich, D. H. J. Org. Chem. 1990, 55, 2895. (c) Ishiwata, H.; Sone, H.; Kigoshi, H.; Yamada, K. J. Org. Chem. 1994, 59, 4712.
[51] Deng, J. G; Hamada, Y; Shioiri, T. Tetrahedron Lett. 1996, 37, 2261.
[52] Li, P.; Xu, J. C. Tetrahedron Lett. 2000,41, 721.
[53] (a)曾加宁，赵玉芬．有机磷试剂在肽合成中的应用．有机化学．1988，8，398．(b)Ramage，R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G W.; Moore, G A. J. Chem. Soc. Perkin Trans. 1. 1985, 461. (c) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. Chem. Soc. Perkin Trans. 1.1985, 1617. (d) Kurz, H.;Angew. Chem., Int. Ed. 1978,17, 67. (e) Jockson, A. G; Kenner, G W.; Moore, G. A.; Ramage, R.; Thorpe, W. D. Tetrahedron Lett. 1976,17, 3621.
[54] (a)黄培强，靳立人，陈安齐．有机合成．北京：高等教育出版社，2004．(b)Hofle，B．G；Steglich, W.; Vorbruggen, H. Angew. Chem., Int. Ed. 1978,17, 569.
[55] (a) Garnet, J. P.; Jacquier, R.; Verducci, J. Tetrahedron.1984,40,1995. (b) Wang, S. S.; Tam, J. P.; Wang, B. S. H.; Merrifield, R. B. J. Peptide Protein Res. 1981,18,459.
[1] (a) Kovalainen, J. T.; Christiaans, J. A. M.; Kotisaari, S.; Laitinen, J. T.; Mannisto, P. T.; Tuomisto, L; Gynther, J. J. Med. Chem. 1999, 42,1193. (b) Appleton, D. R.; Babcock, R. C; Copp, B. R. Tetrahedron. 2001, 57, 10181. (c) Davies, C. E.; Heightman, T. D.; Hennitage, S. A.; Moloney, M. G. Synt.Commun. 1996, 26, 687.
[2] 黄惟德，陈常庆．多肽合成．北京：科学出版社，1985．
[3] (a)Yamada, S. -i.; Takeuchi, Y. Tetrahedron Letters, 1971,12, 3595. (b) Coste, J.; Nguyen, D. L.; Castro, B. Tetrahedron Letters. 1990,31,205. (c) Hofmann, K.; Schmiechen, R.; Wells, R. D.; Wolman, Y.; Yanaihara, N. J. Am. Chem. Soc. 1965,87, 611. (d) Paul, R.; Anderson, G W. J. Am. Chem. Soc. 1960, 82, 4596. (e) Nitecki, D. E.; Halpern, B.; Westley, J.; W. J. Org. Chem. 1968, 33, 864. (f) Kim, S.; Chang, H.; Young, K. K. Tetrahedron Letters. 1985, 26, 1341. (g) Lloyd, K.; Young, G T. J. Chem. Soc. C. 1971,2890.
[4] Williams, M. W.; Young, G T. J. Chem. Soc. 1963,881.
[5] Mohapatra, D. K.; Datta, A. J. Org. Chem. 1999,64,6879.
[6] Otera, J. Esterification: Methods, Reactions and Applications; Wiley-VCH: Weinheim, 2003,303.
[7] (a) Ishihara, K.; Ohara, S.; Yamamoto, H. Science, 2000, 290, 1140. (b) Manabe, K.; Sun, X. M.; Kobayashi, S. J. Am. Chem. Soc. 2001,123,10101.
[8] (a)Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. J. Org. Chem. 2004, 69, 1822. (b) Disadee, W; Watanabe, T.; Ishikawa, T. Synlett. 2003, 115. (c) Isobe, T.; Ishikawa, T. J. Org. Chem. 1999, 64, 6984. (d) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979,52, 1989.
[9] Saito, Y; Yamaki, T.; Kohashi, E; Watanabe, T.; Ouchi, H.; Takahata, H. Tetrahedron Lett. 2005, 46, 1277.
[10] Bartoli, G.; Bosco, M.; Carlone, A.; Dalpozzo, R.; Marcantoni, E.; Melchiorre, P.; Sambri, L. Synthesis. 2007, 3489.
[11] (a) Parrish, J. P.; Salvatore, R. N.; Jung, K. W. Tetrahedron. 2000, 56, 8207. (b) Shaikh, A. A. G; Sivaram, S. Chem. Rev. 1996, 96, 951.
[12] (a)Shiina, I.; Miyoshi, S.; Miyashita, M.; Mukaiyama, T. Chem.Lett. 1994, 515. (b) Shiina, I. Tetrahedron. 2004, 60, 1587.
[13] (a) Shiina, I.; Ibuka, R.; Kubota, M. Chem. Lett. 2002, 286. (b) Nishino, N. J. Synth. Org. Chem. Jpn. 2002, 60, 996. (c) Shiina, I.; Kubota, M.; Ibuka, R. Tetrahedron Lett. 2002, 43, 7535.
[14] Mukaiyama, T.; Funasaka, S. Chem. Lett. 2007,326.
[15] (a) Ishihara, K.; Nakagawa, S.; Sakakura, A. J. Am. Chem. Soc. 2005, 127, 4168. (b) Sakakura, A.; Nakagawa, S.; Ishihara, K. Tetrahedron. 2006, 62,422.
[16] Mercs, L.; Pozzi, G; Quici, S. Tetrahedron Lett. 2007, 48, 3053.
[17] Wakasugi, K.; Misaki, T.; Yamada, K.; Tanabe, Y. Tetrahedron Lett. 2000,41, 5294.
[18] Chen, C. T.; Munot, Y. S. J. Org. Chem. 2005, 70, 8625.
[19] Bartoli, G; Boeglin, J.; Bosco, M.; Locatelli, M.; Massaccesi, M.; Melchiorre, P. Sambri, L. Adv. Synth. Catal. 2005, 347, 33.
[20] Nakayama, M.; Sato, A.; Ishihara, K.; Yamamoto, H. Adv. Synth. Catal. 2004,346,1275.
[21] Mantri, K.; Komura, K.; Sugi, Y. Synthesis. 2005, 1939.
[22] (a) Rama, S.; Lingaiah, N.; Devi, B. L. A. P.; Prasad, R. B. N.; Suryanarayana, I.; Sai Prasad, P. S. Appl. Catal, A. 2004,276, 163. (b) Kawabata, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2003, 44, 9205. (c) Saroja, M.; Kaimol, T. N. B. Synth. Commun. 1986, 1423.
[23] (a) Kantam, M. L.; Bhaskar, V.; Choundary, B. M. Catal. Lett. 2002, 78, 185. (b) Wakasugi, K.; Misaki, T.; Yamada, K.; Tanabe, Y. Tetrahedron Lett. 2000, 41, 5249. (c) Manabe, K.; Iimura, S.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 11971. (d) Hao, X.; Yoshida, A.; Nishikido, J. Tetrahedron Lett. 2004, 45, 781. (e) Wakasugi, K.; Nakamura, A.; Iida, A.; Nishii, Y; Nakatani, N.; Fukushima, S.; Tanabe, Y. Tetrahedron. 2003, 59, 5337. (f) Oohashi, Y; Fukumoto, K.; Mukaiyama, T. Chem. Lett. 2004, 968.
[24] Singleton, V. L.; Bohonos, N.; Ullstrup, A.; Decumbin, J. Nature. 1958,181, 1072.
[25] 刘万云．(+)-Brefeldin A 发酵生产及其衍生物的合成研究(D)．厦门：厦门大学化学系，2006．
[1] Kemp, D. S. The Peptide: Analysis, Synthesis, Biology, Volume 1, E. Gross, J. Meienhoffr (Eds.), Academic Press, New York, 1979,315.
[2] Benoiton, N. L. The Peptide: Analysis, Synthesis, Biology, Volume 5, E. Gross, J. Meienhoffr (Eds.), Academic Press, New York, 1983,217.
[3] (a) Jones, J. H.; Witty, M. J. J. Chem. Soc., Chem. Commun. 1977, 281. (b) Jones, J. H.; Witty, M. J. J. Chem. Soc, Perkin Trans. 1. 1979, 3203. (c) Benoiton, N. L. Biopolymers. 1996, 40, 245.
[4] Benoiton, N. L.; Chen, F. M. F. Peptides: Chemistry and Biology, Marshall, G R (Ed), Escom, Leiden, 1988,152.
[5] Weygand, F.; Steglich, W.; Barocio de la Lama, X. Tetrahedron Suppl. 1966,8,9.
[6] (a)[德]N．休厄德．；H．D．贾库布克著；刘克良，何军林等译．肽：化学与生物学．北京：科学出版社，2005．(b)黄惟德，陈常庆．多肽合成．北京：科学出版社，1985．
[7] (a) Wieland, V. T.; Heinke, B. Liebigs Ann.Chem. 1951, 572,190. (b)Kurz, H. Angew. Chem., Int. Ed. 1978,17,67. (c) Gorecka, A.; Leblawy, M.; Zabrocki, J.; Zwierzak, A. Synthesis 1978,474. (d) Ramage, R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G. W.; Moore, G A. J. Chem. Soc, Perkin Trans. 1. 1985,461. (e) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. J. Chem. Soc, Perkin Trans. 1.1985,1617. (f) Manhas, M. S. Syn.Commun. 1976, 6, 435. (g) Jockson, A. G; Kenner, G W.; Moore, G A.; Ramage, R.; Thorpe, W. D. Tetrahedron Lett. 1976,17, 3627.
[8] (a)赵玉芬，赵国辉，麻远．磷与生命化学.北京：清华大学出版社，2005，68．(b)Feng，Y．P．；Miao，Z．W．；Han，B．；Zhao，Y．F．J. Mol．Catal．A:Chem．2005，239，239．
[9] Sartillo-Piscio, F.; Quintero, L.; Villegas, C; Santacruz-Juarez, E.; Parrodi, C. A. Tetrahedron Lett.2002,43,15.
[10] (a) Amsallem, D.; Gornitzka, H.; Baceiredo, A.; Bertrand, G Angew. Chem. Int. Ed. 1999, 38, 2201. (b) Voitenko, Z.; Mazieres, M. R.; Sanchez, M.; Wolf, J. G. Tetrahedron. 2001, 57, 1059.
[11] (a)曾加宁，赵玉芬．有机磷试剂在肽合成中的应用．有机化学．1988，8，398．(b) Ramage，R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G. W.; Moore, G A. J. Chem. Soc. Perkin Trans. 1. 1985, 461. (c) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. Chem. Soc Perkin Trans. 1. 1985, N6N7. (d) Kurz, H.; Angew. Chem., Int. Ed. 1978, 17, 67. (e) Jockson, A. G; Kenner, G. W.; Moore, G A.; Ramage, R.; Thorpe, W. D. Tetrahedron Lett. 1976,17, 3627.
[N2] Mantri, K.; Komura, K.; Sugi,Y. Synthesis 2005, N939.
[2] Memfield, R. B. J. A. Chem. Soc. 1963,55,2149.
[3] 黄惟德，陈常庆．多肽合成．北京：科学出版社，1985．
[4] (a) Mckay, S. C; Albertson, N. F. J. Am. Chem. Soc. 1957, 79, 4686. (b) Anderson, G W.; Mcgregor, A. G J. Am. Chem. Soc. 1957, 79, 6180.
[5] (a) Carpino, L. A. Acc. Chem. Res. 1987,20,401. (b) Carpino, L. A.; Han, G Y. J. Am. Chem.Soc. 1970, 92, 5748.
[6] Carpino, L. A.; Chao, H. G; Beyermann, M; Bienert, M. J. Org. Chem. 1991, 56,2635.
[7] Carpino, L. A.; Sadat-Aalee, D.; Chao, H. G; Deselms, R. J. Am. Chem. Soc. 1990,112, 9651.
[8] Denkewalter, R. G; Schwarm, H.; Strachan, R. G J. Am. Chem. Soc. 1966,88,3163.
[9] Hirschamann, R.J. Org. Chem. 1967,32, 3415.
[10] (a) Auvin-Guette, C; Frerot, E.; Coste, J.; Rebuffat, S.; Jouin, P.; Bodo, B. Tetrahedron Lett. 1993, 34, 2481. (b) Swain, P. A.; Anderson, B. L.; Goodman, M.; Fuller, W. D. Pept. Res. 1993, 6,147.
[11] (a) Anderson, G W.; Zimmerman, J. F.; Callaham, F. M. J. Am. Chem. Soc. 1966,88, 1334. (b) Anderson, G W.; Zimmerman, J. F.; Callaham, F. M. J. Am. Chem. Soc. 1967,89,5012.
[12] Kurz, H.Angew. Chem., Int. Ed. 1978,17, 67.
[13] Gorecka, A.; Leblawy, M.; Zabrocki, J.; Zwierzak, A. Synthesis 1978,474.
[14] (a) Ramage, R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G W.; Moore, G A. J. Chem. Soc, Perkin Trans. 1.1985,461. (b) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. J. Chem. Soc, Perkin Trans. 1.1985,1617.
[15] Manhas, M. S. Syn. Commun. 1976, 6,435.
[16] Jockson, A. G; Kenner, G W.; Moore, G A.; Ramage, R.; Thorpe, W. D. Tetrahedron Lett. 1976,17, 3627.
[17] Ramage, R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G W.; Moore, G A. J. Chem. Soc, Perkin Trans. 1. 1985,461.
[18] Galpin, I. J.; Robinson, A. E. Tetrahedron Lett. 1984,25, 627.
[19] Galpin, I. J.; Mohammed, A. K.; Patel, A. Tetrahedron. 1988, 44,1685.
[20] (a) Young, R.W.; Wood, K. H.; Joyce, R. J.; Anderson, G W. J. Am. Chem. Soc. 1956, 78, 2126. (b)Crofts, P.C.; Markes, J. H. H.; Rydon, H. N. J. Chem. Soc. 1959,3610.
[21] (a) Tung, R. D.; Rich, D. H. J. Am. Chem. Soc. 1985, 707,4342. (b) Tung, R. D.; Dhaon, M. K.; Rich, D. H. J. Org. Chem. 1986, 57, 3350. (c) Van Der Auwera, C; Van Damme, S.; Anteunis, M. J. O. Int. J. Peptid Protein Res. 1987,29,464.
[22] Van Der Auwera, C; Anteunis, M.J.O. Int J. Peptid Protein Res. 1987,29, 574.
[23] (a) Kisfaludy, L.; Low, M.; Nyeki, O.; Szirtes, R.; Schon, I. Justus Liebigs Ann.Chem. 1973, 1421. (b) Kovacs, J.; Kisfaludy, L.; Ceprini, M. Q. J. Am. Chem. Soc. 1967, 89, 183. (c) Kisfaludy, L. J. Org. Chem. 1970,35, 3565. (d) Kisfaludy, L.; Schon, I.; Szirtes, T; Nyeki, O.; Low, M. Tetrahedron Lett.1914,15,1785. (e) Kisfaludy, L.; Schon, I. Synthesis 1983,325.
[24] Kovacs, J.; Mayers, G L.; Johnson, K. H.; Cover, R. E.; Ghatak, U. R. Chem.Commun. 1970, 53.
[25] (a) Atherton, E.; Cameron, L. R.; Sheppard, R. C. Tetrahedron. 1988, 44, 843. (b) Atherton, E.; Sheppard, R. C. Chem.Commun. 1985, 165. (c) Meldal, M.; Jensen, K. J.; Chem.Commun. 1990,483.
[26] Nefkens, G H. L.; Tesser, G I. J. Am. Chem. Soc. 1961,83, 1263.
[27] (a) Anderson, G W.; Zimmernan, J. E.; Callahan, F. M. J. Am. Chem. Soc. 1963,85, 3039. (b) Anderson, G W.; Zimmernan, J. E.; Callahan, F. M. J. Am. Chem. Soc. 1964, 86, 1839.
[28] (a) Konig, W.; Geiger, R. Chem.Ber. 1970,103, 2024. (b) Konig, W.; Geiger, R. Chem. Ber. 1970,103, 2034.
[29] (a) Atherton, E.; Cameron, L.; Meldal, M.; Sheppard, R. C. Chem.Commun. 1986, 1763. (b) Atherton, E.; Holder, J. L.; Meldal, M.; Sheppard, R. C; Valerio, R. M. J. Chem. Soc, Perkin Trans. 1. 1988, 2887. (c) Breipohl, G; Knolle, J.; Stuber, W. Int. J. Peptide Protein Res. 1989, 34, 262.
[30] Friedrich, R.; Sheppard, R. C; Steglich, W. Chem.Commun. 1987, 1870.
[1] Sheehan, J. C; Hess, G P. J. Am. Chem. Soc. 1955, 77, 1067.
[2] Sarantakis, D.; Teichman, J.; Lien, E. L.; Fenichel, R. Biochem. Biophys. Res. Commun. 1976, 73, 336.
[3] Shechan, J. C; Cruichshank, P. A.; Boshart, G L. J. Org. Chem. 1961,26,2525.
[4] Gibson, F. S.; Park, M. S.; Rapoport, H. J. Org. Chem. 1994, 59, 7503.
[5] Wunsch, E.; Drees, E. Chem, Ber. 1966,99, 110.
[6] Konig, W.; Geiger, R, Chem, Ber. 1970,103,788.
[7] Carpino, L. A. J. Am. Chem. Soc. 1993,115,4397.
[8] Konig, W.; Geiger, R. Chem.Ber.1910,103,2024.
[9] (a) Khorana, H. G; Todd, A. R. J. Chem. Soc. 1953, 2257. (b) Smith, M.; Moffatt, J. G; Khorana, H. G J. Am. Chem. Soc. 1958,80, 6204.
[10] (a) Rebek, J.; Feitler, D. J. Am. Chem. Soc. 1974, 96, 1606. (b) Detar, D. E.; Silverstein, R. J. Am. Chem. Soc. 1966,88,1013.
[11] Hudson, D. J. Org. Chem. 1988, 53, 617.
[12] Weygand, F. Angew.Chem.1963,75 282.
[13] Gawne, G; Kenner, G; Sheppard, R. C. J. Am. Chem. Soc. 1969, 91, 5669.
[14] (a) Yamada, S.; Takeuchi, Y. Tetrahedron Lett.1971, 12, 3595. (b) Wieland, T.; Seeliger, A. Chem, Ber. 1971,104, 3992.
[15] Bates, A. J.; Galpin, I. J.; Hallett, A.; Hudson, D.; Kenner, G. W.; Ramage, R.; Sheppard, R. C. Helv. Chim. Acta. 1975, 58, 688.
[16] Castro, B.; Dormoy, J. R.; Evin, G; Selve, C. Tetrahedron Lett.1975,16, 1219.
[17] (a) Castro, B.; Dormoy, J. R.; Evin, G; Selve, C. J. Chem. Res.(S) 1977, 182. (b) Felix, A. M.; Wang, C. T.; Heimer, E. P.; Fournier, A. Int. J. Pept. Protein Res. 1988, 31, 231. (c) Forest, M.; Fournier, A. Int J .Pept .Protein Res. 1990, 35, 89. (d) Jarrett, J. T.; Lansbury, P. T. Tetrahedron Lett. 1990, 31,4561.
[18] (a) Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett.1990, 31, 205. (b) Hoeg-Jensen, T.; Havsteen, J. M.; Olsen, C. E.; Holm, A. Tetrahedron Lett.1991, 32, 7617.
[19] Campagne, J. M.; Coste, J.; Jouin, P. J. Org. Chem. 1995, 60,5214.
[20] (a) Kim, M. H.; Patel, D. V. Tetrahedron Lett. 1994, 35, 5603. (b) Coste, J.; Campagne, J. M. Tetrahedron Lett. 1995,36,4253.
[21] Coste, J.; Frerot, E.; Jouin, P.; Castro, B. Tetrahedron Lett. 1991,32,1967.
[22] Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. Chem.Commun. 1994,201.
[23] Alsina, J.; Giralt, E.; Albericio, F. Tetrahedron Lett.1996,37,4195.
[24] Coste, J.; Dufour, M. N.; Pantaloni, A.; Castro, B. Tetrahedron Lett.1990,31,669.
[25] Coste, J.; Frerot, E.; Jouin, P. J. Org. Chem. 1994,59,2437.
[26] Frerot, E.; Coste, J.; Pantaloni, A.; Dufour, M. N.; Jouin,P. Tetrahedron.1991,47,259.
[27] (a) Albericio, F.; Cases, M.; Alsina, J.; Triolo, S. A.; Carpino, L. A.; Kates, S. A. Tetrahedron Lett. 1991,38,4853. (b) Han, Y. X.; Albericio, F.; Barany, G J. Org. Chem. 1997, 62,4307. (c) Jou, G; Gonzalez, I.; Albericio, F.; Lloyd-Williams, P.; Giralt, E. J. Org. Chem. 1997, 62, 354. (d) Marsh, I. R.; Bradley, M.; Teague, S. J. Org. Chem. 1997, 62,6199.
[28] Frerot, E.; Coste, J.; Poncet, J.; Jouin, P. Tetrahedron Lett.1992,33,2815.
[29] (a) Dourtoglou, V.; Ziegler, J. C; Gross, B.Tetrahedron Lett.1978, 19, 1269. (b) Dourtoglou, V.; Gross, B.; Lambropoulou, V; Ziodrou, C. Synthesis. 1984, 572.
[30] Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, Tetrahedron Lett.1989,30,1927.
[31] (a) Chen, S.Q.; Xu, J.C. Tetrahedron Lett. 1992, 33, 647. (b) Coste, J.; Frerot, E.; Jouin, P. Tetrahedron Lett. 1991,32, 1967.
[32] Kiso, Y.; Fujiwara, Y; Kimura, T.; Nishitani, A.; Akaji, K. Int. J. Pept. Protein Res. 1992, 40, 308.
[33] (a) Carpino, L. A.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 1994, 35, 2279. (b) Humphrey, J. M.; Aggen, J. B.; Chamberlin, A.R. J. Am. Chem. Soc. 1996, 118, 11759. (c) Wen, J. J.; Spatola, A. F.J.Pept. Res. 1997,49,3.
[34] Ehrlich, A.; Rothemund, S.; Brudel, M.; Beyermann, M.; Carpino, L. A.; Bienert, M. Tetrahedron Lett. 1993,34,4781.
[35] Albericio, F.; Bofill, J. M.; El-Faham, A.; Kates, S. A. J. Org. Chem. 1998, 63, 9678.
[36] Carpino, L. A.; El-Faham, A. J. Org. Chem. 1995, 60, 3561.
[37] Habermann, J.; Kunz, H.; Tetrahedron Lett. 1998,39,265.
[38] Klose, J.; El-Faham, A.; Kenklein, P.; Carpino, L.A.; Bienert, M.; Tetrahedron Lett. 1999,40, 2045.
[39] Story, S. C; Aldrich, J. V. Int. J. Pept. Protein Res. 1994, 43, 292.
[40] Anteunis, M. J. O.; Sharma,N. K. Bull. Soc. Chim. Belg. 1988, 97,281.
[41] (a) Carpino, L. A.; El-Faham, A. J. Am. Chem. Soc. 1995,117, 5401. (b) Vojkovsky, T.; Drake, B. Org.Prep.Proced,Int. 1997,29,497.
[42] El-Faham, A. Chem. Lett. 1998, 671.
[43] Akaji, K.; Kuriyama, N.; Kiso.Y.; Tetrahedron Lett. 1994,35,3315.
[44] (a) Akaji, K.; Hayashi, Y.; Kiso, Y.; Kuriyama, N. J. Org. Chem. 1999, 64,405. (b) Akaji, K.; Tamai, Y; Kiso, Y. Tetrahedron Lett. 1997,53, 567.
[45] (a) Van der Auwera, C; Anteunis, M. J. O. Int. J. Pept. Protein Res. 1987, 29, 574. (b) Van der Auwera, C; Anteunis, M. J. O. Bull. Soc. Chim. Belg. 1986,95,203.
[46] Chen, S. Q.; Xu, J. C. Chin. J. Chem. 1995,13,175.
[47] Chen, S. Q.; Xu, J. C. Tetrahedron Lett. 1991, 32,6711.
[48] (a) Li, H.; Jiang, X.; Ye, Y H.; Fan, C. X.; Romoff, T.; Goodman, M. Org. Lett. 1999,1, 91. (b) Fan, C. X.; Hao, X. L.; Ye, Y. H. Synth, Commun. 1996, 26, 1455.
[49] Belleau, B.; Malek, G J. Am. Chem. Soc. 1968,90,1651.
[50] (a) Tung, R. D.; Dhaon, M. K.; Rich, D. H. J. Org. Chem. 1986, 57, 3350. (b) Colucci, W.J.; Tung, R. D.; Petri, J. A.; Rich, D. H. J. Org. Chem. 1990, 55, 2895. (c) Ishiwata, H.; Sone, H.; Kigoshi, H.; Yamada, K. J. Org. Chem. 1994, 59, 4712.
[51] Deng, J. G; Hamada, Y; Shioiri, T. Tetrahedron Lett. 1996, 37, 2261.
[52] Li, P.; Xu, J. C. Tetrahedron Lett. 2000,41, 721.
[53] (a)曾加宁，赵玉芬．有机磷试剂在肽合成中的应用．有机化学．1988，8，398．(b)Ramage，R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G W.; Moore, G A. J. Chem. Soc. Perkin Trans. 1. 1985, 461. (c) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. Chem. Soc. Perkin Trans. 1.1985, 1617. (d) Kurz, H.;Angew. Chem., Int. Ed. 1978,17, 67. (e) Jockson, A. G; Kenner, G W.; Moore, G. A.; Ramage, R.; Thorpe, W. D. Tetrahedron Lett. 1976,17, 3621.
[54] (a)黄培强，靳立人，陈安齐．有机合成．北京：高等教育出版社，2004．(b)Hofle，B．G；Steglich, W.; Vorbruggen, H. Angew. Chem., Int. Ed. 1978,17, 569.
[55] (a) Garnet, J. P.; Jacquier, R.; Verducci, J. Tetrahedron.1984,40,1995. (b) Wang, S. S.; Tam, J. P.; Wang, B. S. H.; Merrifield, R. B. J. Peptide Protein Res. 1981,18,459.
[1] (a) Kovalainen, J. T.; Christiaans, J. A. M.; Kotisaari, S.; Laitinen, J. T.; Mannisto, P. T.; Tuomisto, L; Gynther, J. J. Med. Chem. 1999, 42,1193. (b) Appleton, D. R.; Babcock, R. C; Copp, B. R. Tetrahedron. 2001, 57, 10181. (c) Davies, C. E.; Heightman, T. D.; Hennitage, S. A.; Moloney, M. G. Synt.Commun. 1996, 26, 687.
[2] 黄惟德，陈常庆．多肽合成．北京：科学出版社，1985．
[3] (a)Yamada, S. -i.; Takeuchi, Y. Tetrahedron Letters, 1971,12, 3595. (b) Coste, J.; Nguyen, D. L.; Castro, B. Tetrahedron Letters. 1990,31,205. (c) Hofmann, K.; Schmiechen, R.; Wells, R. D.; Wolman, Y.; Yanaihara, N. J. Am. Chem. Soc. 1965,87, 611. (d) Paul, R.; Anderson, G W. J. Am. Chem. Soc. 1960, 82, 4596. (e) Nitecki, D. E.; Halpern, B.; Westley, J.; W. J. Org. Chem. 1968, 33, 864. (f) Kim, S.; Chang, H.; Young, K. K. Tetrahedron Letters. 1985, 26, 1341. (g) Lloyd, K.; Young, G T. J. Chem. Soc. C. 1971,2890.
[4] Williams, M. W.; Young, G T. J. Chem. Soc. 1963,881.
[5] Mohapatra, D. K.; Datta, A. J. Org. Chem. 1999,64,6879.
[6] Otera, J. Esterification: Methods, Reactions and Applications; Wiley-VCH: Weinheim, 2003,303.
[7] (a) Ishihara, K.; Ohara, S.; Yamamoto, H. Science, 2000, 290, 1140. (b) Manabe, K.; Sun, X. M.; Kobayashi, S. J. Am. Chem. Soc. 2001,123,10101.
[8] (a)Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. J. Org. Chem. 2004, 69, 1822. (b) Disadee, W; Watanabe, T.; Ishikawa, T. Synlett. 2003, 115. (c) Isobe, T.; Ishikawa, T. J. Org. Chem. 1999, 64, 6984. (d) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979,52, 1989.
[9] Saito, Y; Yamaki, T.; Kohashi, E; Watanabe, T.; Ouchi, H.; Takahata, H. Tetrahedron Lett. 2005, 46, 1277.
[10] Bartoli, G.; Bosco, M.; Carlone, A.; Dalpozzo, R.; Marcantoni, E.; Melchiorre, P.; Sambri, L. Synthesis. 2007, 3489.
[11] (a) Parrish, J. P.; Salvatore, R. N.; Jung, K. W. Tetrahedron. 2000, 56, 8207. (b) Shaikh, A. A. G; Sivaram, S. Chem. Rev. 1996, 96, 951.
[12] (a)Shiina, I.; Miyoshi, S.; Miyashita, M.; Mukaiyama, T. Chem.Lett. 1994, 515. (b) Shiina, I. Tetrahedron. 2004, 60, 1587.
[13] (a) Shiina, I.; Ibuka, R.; Kubota, M. Chem. Lett. 2002, 286. (b) Nishino, N. J. Synth. Org. Chem. Jpn. 2002, 60, 996. (c) Shiina, I.; Kubota, M.; Ibuka, R. Tetrahedron Lett. 2002, 43, 7535.
[14] Mukaiyama, T.; Funasaka, S. Chem. Lett. 2007,326.
[15] (a) Ishihara, K.; Nakagawa, S.; Sakakura, A. J. Am. Chem. Soc. 2005, 127, 4168. (b) Sakakura, A.; Nakagawa, S.; Ishihara, K. Tetrahedron. 2006, 62,422.
[16] Mercs, L.; Pozzi, G; Quici, S. Tetrahedron Lett. 2007, 48, 3053.
[17] Wakasugi, K.; Misaki, T.; Yamada, K.; Tanabe, Y. Tetrahedron Lett. 2000,41, 5294.
[18] Chen, C. T.; Munot, Y. S. J. Org. Chem. 2005, 70, 8625.
[19] Bartoli, G; Boeglin, J.; Bosco, M.; Locatelli, M.; Massaccesi, M.; Melchiorre, P. Sambri, L. Adv. Synth. Catal. 2005, 347, 33.
[20] Nakayama, M.; Sato, A.; Ishihara, K.; Yamamoto, H. Adv. Synth. Catal. 2004,346,1275.
[21] Mantri, K.; Komura, K.; Sugi, Y. Synthesis. 2005, 1939.
[22] (a) Rama, S.; Lingaiah, N.; Devi, B. L. A. P.; Prasad, R. B. N.; Suryanarayana, I.; Sai Prasad, P. S. Appl. Catal, A. 2004,276, 163. (b) Kawabata, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2003, 44, 9205. (c) Saroja, M.; Kaimol, T. N. B. Synth. Commun. 1986, 1423.
[23] (a) Kantam, M. L.; Bhaskar, V.; Choundary, B. M. Catal. Lett. 2002, 78, 185. (b) Wakasugi, K.; Misaki, T.; Yamada, K.; Tanabe, Y. Tetrahedron Lett. 2000, 41, 5249. (c) Manabe, K.; Iimura, S.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 11971. (d) Hao, X.; Yoshida, A.; Nishikido, J. Tetrahedron Lett. 2004, 45, 781. (e) Wakasugi, K.; Nakamura, A.; Iida, A.; Nishii, Y; Nakatani, N.; Fukushima, S.; Tanabe, Y. Tetrahedron. 2003, 59, 5337. (f) Oohashi, Y; Fukumoto, K.; Mukaiyama, T. Chem. Lett. 2004, 968.
[24] Singleton, V. L.; Bohonos, N.; Ullstrup, A.; Decumbin, J. Nature. 1958,181, 1072.
[25] 刘万云．(+)-Brefeldin A 发酵生产及其衍生物的合成研究(D)．厦门：厦门大学化学系，2006．
[1] Kemp, D. S. The Peptide: Analysis, Synthesis, Biology, Volume 1, E. Gross, J. Meienhoffr (Eds.), Academic Press, New York, 1979,315.
[2] Benoiton, N. L. The Peptide: Analysis, Synthesis, Biology, Volume 5, E. Gross, J. Meienhoffr (Eds.), Academic Press, New York, 1983,217.
[3] (a) Jones, J. H.; Witty, M. J. J. Chem. Soc., Chem. Commun. 1977, 281. (b) Jones, J. H.; Witty, M. J. J. Chem. Soc, Perkin Trans. 1. 1979, 3203. (c) Benoiton, N. L. Biopolymers. 1996, 40, 245.
[4] Benoiton, N. L.; Chen, F. M. F. Peptides: Chemistry and Biology, Marshall, G R (Ed), Escom, Leiden, 1988,152.
[5] Weygand, F.; Steglich, W.; Barocio de la Lama, X. Tetrahedron Suppl. 1966,8,9.
[6] (a)[德]N．休厄德．；H．D．贾库布克著；刘克良，何军林等译．肽：化学与生物学．北京：科学出版社，2005．(b)黄惟德，陈常庆．多肽合成．北京：科学出版社，1985．
[7] (a) Wieland, V. T.; Heinke, B. Liebigs Ann.Chem. 1951, 572,190. (b)Kurz, H. Angew. Chem., Int. Ed. 1978,17,67. (c) Gorecka, A.; Leblawy, M.; Zabrocki, J.; Zwierzak, A. Synthesis 1978,474. (d) Ramage, R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G. W.; Moore, G A. J. Chem. Soc, Perkin Trans. 1. 1985,461. (e) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. J. Chem. Soc, Perkin Trans. 1.1985,1617. (f) Manhas, M. S. Syn.Commun. 1976, 6, 435. (g) Jockson, A. G; Kenner, G W.; Moore, G A.; Ramage, R.; Thorpe, W. D. Tetrahedron Lett. 1976,17, 3627.
[8] (a)赵玉芬，赵国辉，麻远．磷与生命化学.北京：清华大学出版社，2005，68．(b)Feng，Y．P．；Miao，Z．W．；Han，B．；Zhao，Y．F．J. Mol．Catal．A:Chem．2005，239，239．
[9] Sartillo-Piscio, F.; Quintero, L.; Villegas, C; Santacruz-Juarez, E.; Parrodi, C. A. Tetrahedron Lett.2002,43,15.
[10] (a) Amsallem, D.; Gornitzka, H.; Baceiredo, A.; Bertrand, G Angew. Chem. Int. Ed. 1999, 38, 2201. (b) Voitenko, Z.; Mazieres, M. R.; Sanchez, M.; Wolf, J. G. Tetrahedron. 2001, 57, 1059.
[11] (a)曾加宁，赵玉芬．有机磷试剂在肽合成中的应用．有机化学．1988，8，398．(b) Ramage，R.; Hopton, D.; Parrott, M. J.; Richardson, R.; Kenner, G. W.; Moore, G A. J. Chem. Soc. Perkin Trans. 1. 1985, 461. (c) Ramage, R.; Atrash, B.; Hopton, D.; Parrott, M. J. Chem. Soc Perkin Trans. 1. 1985, N6N7. (d) Kurz, H.; Angew. Chem., Int. Ed. 1978, 17, 67. (e) Jockson, A. G; Kenner, G. W.; Moore, G A.; Ramage, R.; Thorpe, W. D. Tetrahedron Lett. 1976,17, 3627.
[N2] Mantri, K.; Komura, K.; Sugi,Y. Synthesis 2005, N939.