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化学学报
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化学学报 ›› 1978, Vol. 36 ›› Issue (4): 1-8.    下一篇

论文

D-18-甲基炔诺酮及D-18-甲基二烯炔诺酮的全合成

甾族激素组   

  1. 中国科学院上海有机化学研究所
  • 投稿日期:1978-01-24 发布日期:2013-06-03

TOTAL SYNTHESES OF D-NORGESTREL AND D-13-ETHYL NORGESTRIENONE

STEROID HORMONE GROUP   

  1. Shanghai Institute of Organic Chemistry, Academia Sinica
  • Received:1978-01-24 Published:2013-06-03

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本文报导了采用微生物啤酒酵母菌(2.346)用18-甲基-3-甲氧基-8,14-开环-Δ1,3,5(10)9(11)-雌甾四烯-14,17-双酮(Ⅲ)为原料进行不对称还原得到光学活性的18-甲基-3-甲氧基-8,14-开环-Δ1,3,5(10)9(11)-雌甾四烯17β-羟基-14-酮(Ⅳ),用Ⅳ按已知法分别合成了目的物Ⅰ和Ⅱ.Ⅰ和Ⅱ经药理试验证明其抗生育效果比两者的消旋化合物强一倍.

The asymmetric miorobiologioal rednotion of the prochiral 13-ethyl-3-methoxy-8,14-seco-Δ1,3,5(10)9(11)-estratetraen-14，17-dione (Ⅲ) with Saccharomyces cerevisirae (2.346) was suoressful to afford an optical active key intermediate IV in an excellent yield.The D-norgestrel (Ⅰ) and D-13-ethyl norgestrienone (Ⅱ) were synthesized from this optically active intermediate (N) via 8-step and 11-step routes, the total yields amounted to 36.6 and 10%，respectively.