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化学学报
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化学学报 ›› 1980, Vol. 38 ›› Issue (1): 78-83. 上一篇    下一篇

论文

用有机铜试剂的1, 4-加成反应合成11-去羟前列腺素E1及其15(R, S)-甲基衍生物

刘志煜   

  1. 中国科学院上海有机化学研究所
  • 投稿日期:1978-04-13 发布日期:2013-06-03

SYNTHESIS OF dl-11-DEOXYPROSTAGLANDIN E1 AND ITS 15 (R, S)-15-METHYL DERIVATIVE BY 1, 4-ADDITION OF AN ORGANOCOPPER REAGENT

LIU ZHI-YU   

  1. Shanghai Institute of Organic Chemistry, Acadimia Sinica
  • Received:1978-04-13 Published:2013-06-03

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本文报告用有机铜的1,4-加成反应来合成标题化合物。正丁基锂-N,N,N',N'-四甲基乙二胺复合物1在乙醚溶液中,于-70℃与烯碘化合物3反应得到高产率烯锂化合物4。从后者制备的有机铜试剂与化合物6反应,经层析后得到80～85%的dl-11-去羟前列腺素E1甲酯7a及其15-表异构物7b。同样,从11制备的有机铜试剂与化合物6反应得到39%的dl-15(R,S)-11-去羟-15-甲基前列腺素E1甲酯。

Synthesis of the tit1e compounds by 1,4-addition of an organocopper reagent is described.The reaction of n-butyllithium-N,N,N',N'-tetramethylethylene diamine complex 1 and the iodovinyl compound 3 in ethyl ether at -70℃ affords in high yield the vinyllithium compound 4.The organocopper reagent 5,prepared from 4,reacted with 6 to afford after chromatography the dl-11-deoxy-PGE1 methyl ester 7a and its 15-epimer 7b in 80 -85% yield.Similarly,the organocopper reagent 13 prepared from 11,reacted with 6 to give dl-15(R,S)-11-deoxy-15-methyl-PGE1 methyl ester in 39% yield.