综述与进展

加兰他敏类生物碱的不对称合成研究进展

  • 王海明 ,
  • 陈鹏 ,
  • 唐萌
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  • a 兰州大学药学院 兰州 730000;
    b 吉林大学化学学院 无机合成与制备化学国家重点实验室 长春 130012

收稿日期: 2013-12-02

  修回日期: 2014-01-07

  网络出版日期: 2014-02-10

基金资助

国家自然科学基金(No. 21302061)、中国博士后科学基金(Nos. 2013T60318,2012M510130)和吉林省科技发展计划(No. 20140520084JH)资助项目.

Progress in Asymmetric Synthesis of Galanthamine-Type Alkaloids

  • Wang Haiming ,
  • Chen Peng ,
  • Tang Meng
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  • a School of Pharmacy, Lanzhou University, Lanzhou 730000;
    b State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012

Received date: 2013-12-02

  Revised date: 2014-01-07

  Online published: 2014-02-10

Supported by

Project supported by the National Natural Science Foundation of China (No. 21302061), the China Postdoctoral Science Foundation (Nos. 2013T60318, 2012M510130) and the Jilin Province Science and Technology Development Plan Item (No. 20140520084JH).

摘要

加兰他敏类生物碱是氢化二苯并呋喃类生物碱的重要组成部分. 它们独特的结构、良好的生物活性和前景广阔的药用价值吸引了众多化学家和药物学家的兴趣. 其合成难点是其中的含芳基手性全碳季碳的构筑. 本综述旨在阐述到目前为止加兰他敏类生物碱的不对称合成方法,根据合成路线中手性季碳的构筑方式分类进行说明,并尝试对每种合成方法进行评述.

本文引用格式

王海明 , 陈鹏 , 唐萌 . 加兰他敏类生物碱的不对称合成研究进展[J]. 有机化学, 2014 , 34(5) : 852 -864 . DOI: 10.6023/cjoc201312002

Abstract

Galanthamine-type alkaloids are an important type of hydrodibenzofuran alkaloids. Their unique intriguing structures, significant biological activitives and pharmacological potential have attracted much attention of chemists and pharmacologists. The major challenge for their synthesis is how to construct the aryl-substituted all-carbon quaternary stereogenic center. In this paper, current strategies for asymmetric synthesis of galanthamine-type alkaloids are reviewed, and the different methods to prepare the quaternary carbon are discussed. The features of different strategies are also commented.

参考文献

[1] Proskurnina, N. F.; Yakoleva, A. P. J. Gen. Chem. 1952, 22, 1899.



[2] (a) Han, S. Y.; Sweeney, J. E.; Bachman, E. S.; Schweiger, E. J.; Forloni, G.; Coyle, J. T.; Davis, B. M.; Joullie, M. M. Eur. J. Med. Chem. 1992, 27, 673。



(b) Marco-Contelles, J.; do Carmo Carreiras, M.; Rodriguez, C.; Villarroya, M.; Garcia, A. G. Chem. Rev. 2006, 106, 116.



[3] (a) Boers, G. M.; Kosley, R. W. Drugs Future 1996, 21, 621.



(b) Rainer, M. Drugs Today 1997, 33, 273.



(c) Mucke, H. A. M. Drugs Today 1997, 33, 259.



(d) Giacobini, E. Neurochem. Int. 1998, 32, 413.



(e) Weinstock, M. CNS Drugs 1999, 12, 307.



(f) Sramek, J. J.; Frackiewicz, E. J.; Cutler, N. R. Expert Opin. Investig. Drugs 2000, 9, 2393.



[4] Lilienfeld, S. CNS Drug Rev. 2002, 8, 159.



[5] Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 433.



[6] (a) Fan, C. A.; Tu, Y. Q.; Song, Z. L.; Zhang, E.; Shi, L.; Wang, M.; Wang, B.; Zhang, S. Y. Org. Lett. 2004, 6, 4691.



(b) Hu, X. D.; Tu, Y. Q.; Zhang, E.; Gao, S.; Wang, S.; Wang, A.; Fan, C. A.; Wang, M. Org. Lett. 2006, 8, 1823.



[7] Chen, J. Q.; Xie, J. H.; Bao, D. H.; Liu, S.; Zhou, Q. L. Org. Lett. 2012, 14, 2714.



[8] Chen, P.; Bao, X.; Zhang, L. F.; Ding, M.; Han, X. J.; Li, J.; Zhang, G. B.; Tu, Y. Q.; Fan, C. A. Angew. Chem. Int. Ed. 2011, 50, 8161.



[9] (a) Parker, K. A.; Fokas, D. J. Am. Chem. Soc. 1992, 114, 9688.



(b) Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028.



(c) Taber, D. F.; Neubert, T. D.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12416.



(d) Stork, G.; Yamashita, A.; Adams, J.; Schulte, G. R.; Chesworth, R.; Miyazaki, Y.; Farmer, J. J. J. Am. Chem. Soc. 2009, 131, 11402.



(e) He, Z.-L.; Wu, Y.-L.; Hong, Y.-S.; Wu, Y.-K.; Yao, Z.-J. Total Synthesis of Natural ProductsAlkaloids, Science Press, Beijing, 2009 (in Chinese).



(何子乐, 吴毓林, 洪永叁, 伍贻康, 姚祝军, 天然产物全合成荟萃——生物碱, 科学出版社, 北京, 2009.)



[10] (a) Gong, J.; Lin, G.; Sun, W.; Li, C. C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 16745.



(b) Peng, F.; Danishefsky, S. J. J. Am. Chem. Soc. 2012, 134, 18860.



(c) Lu, P.; Gu, Z.; Zakarian, A. J. Am. Chem. Soc. 2013, 135, 14552.



[11] Cha, J. Y.; Yeoman, J. T.; Reisman, S. E. J. Am. Chem. Soc. 2011, 133, 14964.



[12] (a) Marco-Contelles, J.; Perez-Mayoral, E.; van Nhien, A. N.; Postel, D. Targets Heterocycl. Syst. 2007, 11, 365.



(b) Fang, L.; Gou, S. H.; Zhang, Y. H. Chin. J. Org. Chem. 2011, 31, 286 (in Chinese).



(房雷, 苟少华, 张奕华, 有机化学, 2011, 31, 286.)



[13] Shieh, W.-C.; Carlson, J. A. J. Org. Chem. 1994, 59, 5463.



[14] Magnus, P.; Sane, N.; Fauber, B. P.; Lynch, V. J. Am. Chem. Soc. 2009, 131, 16045.



[15] (a) Kametani, T.; Sivaraman Premila, M.; Fukumoto, K. Heterocycles 1976, 4, 1111.



(b) Szewczyk, J.; Wilson, J. W.; Lewin, A. H.; Carroll, F. I. J. Heterocycl. Chem. 1995, 32, 195.



(c) Chaplin, D. A.; Johnson, N. B.; Paul, J. M.; Potter, G. A. Tetrahedron Lett. 1998, 39, 6777.



[16] (a) Barton, D. H. R.; Kirby, G. W. J. Chem. Soc. 1962, 806.



(b) Barton, D. H. R.; Kirby, G. W.; Taylor, J. B.; Thomas, G. M. J. Chem. Soc. 1963, 4545.



(c) Fuganti, C. Chim. Ind. (Milan) 1969, 51, 1254.



(d) Bhandarkar, J. G.; Kirby, G. W. J. Chem. Soc. (C) 1970, 1224.



(e) Eichhorn, J.; Takada, T.; Kita, Y.; Zenk, M. H. Phytochemistry 1998, 49, 1037.



[17] (a) Tomioka, K.; Shimizu, K.; Yamada, S.-I.; Koga, K. Heterocycles 1977, 6, 1752.



(b) Shimizu, K.; Tomioka, K.; Yamada, S.-I.; Koga, K. Heterocycles 1977, 8, 277.



(c) Shimizu, K.; Tomioka, K.; Yamada, S.-I.; Koga, K. Chem. Pharm. Bull. 1978, 26, 3765.



[18] (a) Kodama, S.; Hamashima, Y.; Nishide, K.; Node, M. Angew. Chem., Int. Ed. 2004, 43, 2659.



(b) Node, M.; Kodama, S.; Hamashima, Y.; Katoh, T.; Nishide, K.; Kajimoto, T. Chem. Pharm. Bull. 2006, 54, 1662.



[19] Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 11262.



[20] (a) Trost, B. M.; Tang, W. Angew. Chem., Int. Ed. 2002, 41, 2795.



(b) Trost, B. M.; Tang, W.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 14785.



[21] Zang, Y.; Ojima, I. J. Org. Chem. 2013, 78, 4013.



[22] Satcharoen, V.; McLean, N. J.; Kemp, S. C.; Camp, N. P.; Brown, R. C. Org. Lett. 2007, 9, 1867.



[23] Kim, Y.-J.; Tae, J. Synlett 2006, 61.



[24] Choi, J.; Kim, H.; Park, S.; Tae, J. Synlett 2013, 379.



[25] Malachowski, W. P.; Paul, T.; Phounsavath, S. J. Org. Chem. 2007, 72, 6792.



[26] Tanimoto, H.; Kato, T.; Chida, N. Tetrahedron Lett. 2007, 48, 6267.



[27] Imuta, S.; Tanimoto, H.; Momose, M. K.; Chida, N. Tetrahedron 2006, 62, 6926.



[28] Kato, T.; Tanimoto, H.; Yamada, H.; Chida, N. Heterocycles 2010, 82, 563.

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