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有机化学 ›› 2014, Vol. 34 ›› Issue (9): 1793-1799.DOI: 10.6023/cjoc201404033 上一篇    下一篇

研究论文

碳正离子重排反应合成Cyclocitrinol核心骨架（约稿）

刘涛a, 严语波b, 马海燕a, 丁凯c   

  1. a 华东理工大学金属有机 实验室, 上海 200237;
    b 上海师范大学资源化学实验室, 上海 200234;
    c 中国科学院上海有机化学研究所, 天然产物合成重点实验室, 上海 200032
  • 收稿日期:2014-04-17 修回日期:2014-05-13 发布日期:2014-05-23
  • 通讯作者: 马海燕, 丁凯 E-mail:dingkai@mail.sioc.ac.cn
  • 基金资助:

    国家自然科学青年科学基金(No. 20902098)资助项目.

Synthesis of Cyclocitrinol Skeleton via a Carbocation Rearrangement

Liu Taoa, Yan Yubob, Ma Haiyana, Ding Kaic   

  1. a Laboratory of Organometallic, East China University of Science and Technology, Shanghai 200237;
    b Laboratory of Resource Chemistry, Shanghai Normal University, Shanghai 200234;
    c Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2014-04-17 Revised:2014-05-13 Published:2014-05-23
  • Supported by:

    Project supported by the National Natural Science Foundation for Young Scientists of China (No. 20902098).

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Cyclocitrinol是一类具有独特的桥环结构的天然产物，其桥环核心骨架可由高张力的降蒈烯酮开环制备得到. 以商品化的19-羟基雄甾为原料，通过高烯丙基碳正离子重排反应，高效地合成了降蒈烯酮关键中间体，完成了Cyclocitrinols天然产物的核心骨架的合成.

关键词: 甾体, Mitsunobu反应, Cyclocitrinol, 碳正离子重排

Cyclocitrinol featured a unique bridged bicyclic skeletons, which may be constructed via SmI2-mediated reaction from a highly strained norcarenone. Herein, using commercially available 19-hydroxy-androstane as starting material, the norcarenone intermediate was synthesized via a novel homoallylic carbocation rearrangement, which was transformed into the core of cyclocitrinols.

Key words: steroids, mitsunobu reaction, cyclocitrinol, carbocation rearrangement