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化学进展 2011, Vol. 23 Issue (10): 2065-2078 前一篇   后一篇

• 综述与评论 •

海洋二聚吡咯-咪唑类生物碱

王珏, 詹岳雄, 姜标*   

  1. 中国科学院上海有机化学研究所 天然产物有机合成化学重点实验室 上海 200032
  • 收稿日期:2011-03-01 修回日期:2011-04-01 出版日期:2011-10-24 发布日期:2011-09-15
  • 作者简介:e-mail:jiangb@mail.sioc.ac.cn
  • 基金资助:

    国家重点基础研究发展计划(973)项目(No.2010CB833200,2010CB833302)、国家科技重大专项项目(No.2009ZX09501)和国家自然科学基金重点项目(No. 20832007) 资助

Dimeric Pyrrole-Imidazole Alkaloids

Wang Jue, Zhan Yuexiong, Jiang Biao*   

  1. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
  • Received:2011-03-01 Revised:2011-04-01 Online:2011-10-24 Published:2011-09-15

近20年来,大量二聚吡咯-咪唑类生物碱从海绵中分离得到,并表现出良好的生理活性。而这些分离上的进展,为确定该类化合物结构提供新的信息,更促进了生源合成的研究发展。这类化合物因其结构新颖性、多样性以及良好的生理活性而成为合成化学家们关注的焦点。由于该类天然产物分子结构的复杂性、分子中的高氮数(N/C ≈ 1 ∶2)以及不确定的绝对构型,使得这类分子的合成十分具有挑战性。本文主要综述了海洋二聚吡咯-咪唑类生物碱的分离和合成进展。

Over the last two decades, numerous dimeric pyrrole-imidazole alkaloids have been isolated from marine sponges, and exhibit exciting bioactivities. This may lead to new ideas for biomimetic total synthesis of this group of natural molecules even in advance of their identification and characterization. The interest of organic chemists in the total synthesis of the pyrrole-imidazole alkaloids has strongly increased because of their structural novelty, molecular diversity, and promising biological activities. Challenges are also plentiful from a synthetic point of view. Architectural complexity, unusually high nitrogen content (N/C ≈ 1 ∶2), unknown absolute stereochemistry are just some of the dreadful aspects one has to take into account while planning a total synthesis of these alkaloids. This article will account for the recent progress in achieving the total synthesis of these pyrrole-imidazole dimers.

Contents
1 Introduction
2 Classification of pyrrole-imidazole alkaloids
3 Synthesis of pyrrole-imidazole dimers
3.1 Nagelamide D
3.2 Mauritiamine
3.3 Sceptrin
3.4 Ageliferin
3.5 Axinellamines and massadine
3.6 Palau'amine
3.7 New dimers without reports
4 Conclusions and outlook

中图分类号: 

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海洋二聚吡咯-咪唑类生物碱