化学学报 ›› 1997, Vol. 55 ›› Issue (6): 611-616. 上一篇    下一篇

研究论文

用反Diels-Alder反应合成天然产物XIV. 立体控制合成(±)-环 氧菌素和(±)- 4-表环氧菌素

刘志煜;李恒光;陈淑华   

  1. 中国科学院上海有机化学研究所.上海(200032);四川大学化学系.成都(610064)
  • 发布日期:1997-06-15

Natural products synthesis by retro Diels-Alder reaction XIV. Stereospecific synthesis of (±)-epoformin and (± )-epiepoformin

Liu Zhiyu;Li Hengguang;Chen Shuhua   

  1. Shanghai Inst Organ Chem., CAS.Shanghai(200032);Sichuan Univ, Dept Chem.Chengdu(610064)
  • Published:1997-06-15

对苯醌与环戊二烯经Diels-Alder反应保护其一侧的双键,在引入必要的官能团及取代基后,再经反Diels-Alder反应得到(±)-4-表环氧菌素(7),对7进一步进行羟基构型转换而得(±)-环氧菌素(6)。总产率分别为70%和65%。

关键词: 立体控制反应, 天然产物, 迪尔斯-阿尔德反应, 环氧菌素, 表环氧菌素, 环戊二烯, 苯醌

p-Benzoquinone reacted with cyclopentadiene to mask its double bond. After introduction of the necessary functional groups and substituent, retro Diels-Alder reaction gave (± )-epiepoformin, which was converted into (±)-epoformin by inversion of its hydroxy configuration in 70% and 65% overall yields, respectively.

Key words: NATURAL PRODUCTS, DIELS-ALDER REACTION, CYCLOPENTADIENE, BENZOQUINONE

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