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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (10): 1668-1671. 上一篇    下一篇

研究简报

6-烯-8-羰基-1-叔丁氧基羰基氮杂螺[4,4]壬烷的合成

孙默然 卢宏涛 杨 华   

  1. (郑州大学药学院 郑州 450001)
  • 收稿日期:2008-12-01 修回日期:2009-03-15 发布日期:2009-06-01

Synthesis of 1-Aza-1-(t-butoxycarbonyl)-8-oxo-spiro[4,4]non-6-ene

Sun, Moran   Lu, Hongtao   Yang, Hua*   

  1. (School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001)
  • Received:2008-12-01 Revised:2009-03-15 Published:2009-06-01

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以烯丙基脯氨酸甲酯(1)为起始原料, 经7步反应以42%的总收率得到了三尖杉碱合成中的重要中间体6-烯-8-羰基-1-叔丁氧基羰基氮杂螺[4,4]壬烷(7). 关键反应为构筑螺环季碳的[2,3]斯蒂文森重排(Stevens rearrangement)及烯丙基双键加氧的酸内酯化反应(Acid-lactonization reaction).

关键词: 三尖杉碱, 斯蒂文森重排, 酸内酯化, 螺内酯

1-Aza-1-(t-butoxycarbonyl)-8-oxo-spiro[4,4]non-6-ene (7), one of the key intermediates in the preparation of cephalotaxine, was conveniently synthesized in 42% overall yield with the Stevens rearrangement and acid-lactonization as key steps.

Key words: cephalotaxine, Stevens rearrangement, acid-lactonization, spirolactone