Statine及其类似物不对称合成研究进展
收稿日期: 2012-07-20
修回日期: 2012-08-29
网络出版日期: 2012-09-03
基金资助
国家自然科学基金(No. 81001392)、复旦大学新教师科研启动基金(No. 10FX070)和复旦大学药学院新教师科研启动基金资助项目.
Progress in the Asymmetric Synthesis of Statine and Its Analogs
Received date: 2012-07-20
Revised date: 2012-08-29
Online published: 2012-09-03
Supported by
Project supported by the National Natural Science Foundation of China (No. 81001392), the Fundamental Research Funds for the Central Universities (No. 10FX070), and the School of Pharmacy, Fudan University.
张伟 . Statine及其类似物不对称合成研究进展[J]. 有机化学, 2012 , 32(12) : 2203 -2213 . DOI: 10.6023/cjoc201207029
Statine and its analogs are special kind of β-hydroxy-γ-amino acids, which are usually core segments in many bioactive compounds. In this paper, several synthetic strategies are summarized.
Key words： statine; β-hydroxy-γ-amino acid; asymmetric synthesis
[1] Umezawa, H.; Aoyagi, T.; Morishima, H.; Matauzaki, H.; Hamada, M.; Takeuchi, T. J. Antibiot. 1970, 23, 259.
[2] Rinehart, K. L.; Gloer, J. B.; Cook, J. C.; Mizsak, S. A.; Scahill, T. A. J. Am. Chem. Soc. 1981, 103, 1857.
[3] Pettit, G. R.; Kamano, Y.; herald, C. L.; Tuinman, A. A.; Boettner, F. E.; Kizu, H.; Schmidt, J. M.; Baczynskyj, L.; Tomer, K. B.; Bontems, R. J. J. Am. Chem. Soc. 1987, 109, 6883.
[4] Stratmann, K.; Burgoynem, L.; Moore, R. E.; Patterson, G. M. L. J. Org. Chem. 1994, 59, 7219.
[5] Boger, D. L.; Colletti, S. L.; Horda, T.; Menezes, R. F. J. Am. Chem. Soc. 1994, 116, 5607.
[6] Rich, D. H.; Sun, E. T.; Boparai, A. S. J. Org. Chem. 1978, 43, 3624.
[7] Rittle, K. E.; Homnick, C. F.; Ponticello, G. S.; Evans, B. E. J. Org. Chem. 1982, 47, 3016.
[8] Sham, H. L.; Rempel, C. A.; Stein, H.; Cohen, J. J. Chem. Soc., Chem. Commun. 1987, 683.
[9] Hanson, G. J.; Baran, J. S.; Lindberg, T. Tetrahedron Lett. 1986, 27, 3577.
[10] Pettit, G. R.; Singh, S. B.; Srirangam, J. K.; Pierson-Hogan, F.; Williams, M. D. J. Org. Chem. 1994, 59, 1796.
[11] Takemoto, Y.; Matsumoto, T.; Ito, Y.; Terashima, S. Tetrahedron Lett. 1990, 31, 217.
[12] Mikami, K.; Kaneko, M.; Loh, T.-P. Tetrahedron Lett. 1990, 31, 3909.
[13] Kiyooka, S.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 34, 5729.
[14] Andrés, J. M.; Pedrosa, R.; Pérez, A.; Pérez-Encabo, A. Tetrahedron 2001, 57, 8521.
[15] Nelson, C. G.; Burke, T. R. Jr. J. Org. Chem. 2012, 77, 733.
[16] Devant, R. M.; Radunz, H. E. Tetrahedron Lett. 1988, 29, 2307.
[17] Rivero, R. A.; Greenlee, W. J. Tetrahedron Lett. 1991, 32, 2453.
[18] Cooke, J. W. B.; Davies, S. G.; Naylor, A. Tetrahedron 1993, 49, 7955.
[19] Woo, P. W. K. Tetrahedron Lett. 1985, 26, 2973.
[20] Reetz, M. T.; Rivadeneira, E.; Niemeyer, C. Tetrahedron Lett. 1990, 31, 3863.
[21] Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
[22] Tsukamoto, M.; Iio, H.; Tokoroyama, T. Tetrahedron Lett. 1985, 26, 4471.
[23] Iio, H.; Mizobuchi, T.; Tsukamoto, M.; Tokoroyama, T. Tetrahedron Lett. 1986, 27, 6373.
[24] Tsukamoto, M.; Iio, H.; Tokoroyama, T. Tetrahedron Lett. 1987, 28, 4561.
[25] Franciotti, M.; Mann, A.; Taddei, M. Tetrahedron Lett. 1991, 32, 6783.
[26] Veeresha, G.; Datta, A. Tetrahedron Lett. 1997, 38, 5223.
[27] Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1990, 31, 1803.
[28] Maibaum, J.; Rich, D. H. J. Org. Chem. 1988, 53, 869.
[29] Harris, B. D.; Joullié, M. M. Tetrahedron 1988, 44, 3489.
[30] Dufour, M.-N.; Jouin, P.; Poncet, J.; Pantaloni, A.; Castro, B. J. Chem. Soc., Perkin Trans. 1 1986, 1895.
[31] Kessler, H.; Schudok, M. Synthesis 1990, 457.
[32] Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474.
[33] Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531.
[34] Nishi, T.; Kitamura, M.; Ohkuma, T.; Noyori, R. Tetrahedron Lett. 1988, 29, 6327.
[35] Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl. 1988, 27, 426.
[36] Ma, D.; Ma, J.; Ding, W.; Dai, L. Tetrahedron: Asymmetry 1996, 7, 2365.
[37] Maibaum, J.; Rich, D. H. J. Med. Chem. 1989, 32, 1571.
[38] Jouin, P.; Castro, B. J. Chem. Soc., Perkin Trans. 1 1987, 1177.
[39] Xiao, K.; Wang, X.; Shen, J.-K. Chin. J. Synth. Chem. 2006, 14, 373 (in Chinese).
(肖坤, 王昕, 沈竞康, 合成化学, 2006, 14, 373.)
[40] Cadicamo, C. D.; Asante, V. A.; Ammar, M. A.; Borelli, C.; Korting, H. C.; Koksch, B. J. Pept. Sci. 2009, 15, 272.
[41] Fehrentz, J.-A.; Bourdel, E.; Califano, J.-C.; Chaloin, O.; Devin, C.; Garrouste, P.; Lima-Leite, A.-C.; Llinares, M.; Rieunier, F.; Vizavonna, J.; Winternitz, F.; Loffet, A.; Martinez, J. Tetrahedron Lett. 1994, 35, 1557.
[42] Fehreztz, J.-A.; Genu-Dellac, C.; Amblard, M.; Winternitz, F.; Loffet, A.; Martinez, J. J. Pept. Sci. 1995, 1, 124.
[43] Poncet, J.; Jouin, P.; Castro, B. J. Chem. Soc., Perkin Trans. 1 1990, 611.
[44] Klutchko, S.; O'Brien, P.; Hodges, J. C. Synth. Commun. 1989, 19, 2573.
[45] Katsuki, T.; Ymaguchi, M. Bull. Chem. Soc. Jpn. 1976, 49, 3287.
[46] Galeotti, N.; Poncet, J.; Chiche, L.; Jouin, P. J. Org. Chem. 1993, 58, 5370.
[47] Schmidt, U.; Riedl, B.; Haas, G.; Griesser, H.; Vetter, A.; Weinbrenner, S. Synthesis 1993, 216.
[48] Ishizuka, T.; Ishibuchi, S.; Kunieda, T. Tetrahedron 1993, 49, 1841.
[49] Yamamoto, T.; Ishibuchi, S.; Ishizuka, T.; Haratake, M.; Kunieda, T. J. Org. Chem. 1993, 58, 1997.
[50] Kano, S.; Yuasa, Y.; Yokomatsu, T.; Shibuya, S. J. Org. Chem. 1988, 53, 3381.
[51] Kano, S.; Yuasa, Y.; Yokomatsu, T.; Shibuya, S. J. Org. Chem. 1988, 53, 3865.
[52] Sakaitani, M.; Ohfune, Y. J. Am. Chem. Soc. 1990, 112, 1150.
[53] Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1987, 28, 3987.
[54] Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359.
[55] Bernardi, A.; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Tetrahedron Lett. 1990, 31, 4949.
[56] Koot, W.-J.; Ginkel, R.; Dranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 401.
[57] He, B.-Y.; Wu, T.-J.; Yu, X.-Y.; Huang, P.-Q. Tetrahedron: Asymmetry 2003, 14, 2101.
[58] Luo, J.-M.; Dai, C.-F.; Lin, S.-Y.; Huang, P.-Q. Chem. Asian J. 2009, 4, 328.
[59] Huang, P. Q.; Wang, S. L.; Ye, J. L.; Ruan, Y. P.; Huang Y. Q.; Zheng H. Z.; Goa, J. X. Tetrahedron 1998, 54, 12547.
[60] Ohta, T.; Shiokawa, S.; Sakamoto, R.; Nozoe, S. Tetrahedron Lett. 1990, 31, 7329.
[61] Catasús, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1999, 40, 9309.
[62] Bertelli, L.; Fiaschi, R.; Napolitano, E. Gazz. Chim. Ital. 1993, 123, 521.
[63] Bessodes, M. S. M.; Antonakis, K. Tetrahedron: Asymmetry 1991, 2, 111.
[64] Cestejón, P.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1996, 52, 7063.
[65] Bessodes, M.; Saïah, M.; Antonakis, K. J. Org. Chem. 1992, 57, 4441.
[66] Maier, M. E.; Hermann, C. Tetrahedron 2000, 56, 557.
[67] Hermann, C.; Giammasi, C.; Geyer, A.; Maier, M. E. Tetrahedron 2001, 57, 8999.
[68] Castejón, P.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron 1996, 52, 7063.
[69] Ko, S. Y. J. Org. Chem. 2002, 67, 2689.
[70] Kondekar, N. B.; Kandula, R. S. V.; Kumar, P. Tetrahedron Lett. 2004, 45, 5477.
[71] Danishefsky, S.; Kobayashi, S.; Kerwin, J. F. J. Org. Chem. 1982, 47, 1983.
[72] Midland, M. M.; Afonso, M. M. J. Am. Chem. Soc. 1989, 111, 4368.
[73] Kawabata, T. K.; Kiryu, Y.; Sugiura, Y.; Fuji, K. Tetrahedron Lett. 1993, 34, 5127.
[74] Takahata, H.; Yamazaki, K.; Takamatsu, T.; Yamazaki, T.; Momose, T. J. Org. Chem. 1990, 55, 3947.
[75] Williams, R. M.; Closon, P.-J.; Zhai, W. Tetrahedron Lett. 1994, 35, 9371.
[76] Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959.
[77] Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210.
[78] Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219.
[79] Ghosh, A. K.; Shurrush, K.; Kulkarni, S. J. Org. Chem. 2009, 74, 4508.
[80] Bäck, M.; Nyhlén, J.; Kvarnström, I.; Appelgren, S.; Borkakoti, N.; Jansson, K.; Lindberg, J.; Nyström, S.; Hallberg, A.; Rosenquist, Å.; Samuelsson, B. Bioorg. Med. Chem. 2008, 16, 9471.
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