Acta Chimica Sinica ›› 1980, Vol. 38 ›› Issue (4): 371-376. Previous Articles     Next Articles

15(R,S)-dl-ω-乙基-13,14-去氢前列腺素F的合成

褚季瑜1, 鲁秀英1, 方雪君1, 阮尚冏2, 李志源2   

  1. 1. 上海化工学院制药教研组;
    2. 上海第九制药厂中心试验室
  • 收稿日期:1978-10-18 出版日期:1980-07-15 发布日期:2013-06-03

SYNTHESIS OF 15(R, S)-dl-ω-ETHYL-13, 14-DEHYDRO PROSTAGLANDIN F

CHU JI-YU1, LU XIU-YING1, FANG XUE-JUN1, RUAN SHANG-JIONG2, LI ZHI-YUAN2   

  1. 1. Shanghai College of Chemical Engineering;
    2. Shanghai No.9 Pharmaceutical Works
  • Received:1978-10-18 Online:1980-07-15 Published:2013-06-03

A new prostaglandin analog 15(R, S)-dl-ω-ethyl-13, 14-dehydro-prostaglandin F (10) has been synthesized from dl-epoxide 4 via a five-step process.The key reaction step involved in this synthesis was the formation of compound 5 which was prepared from 4 with ethylmethoxy aluminum reagent 3.Molecular oxygen in presence of Pt transformed 5 to the lactone 6.6 was reduced to 7 by diieobutylaluminum hydride.Product 10 was finally obtained from dealkylation of compound 9 which was prepared by means of Wittig reaction.Alternatively activated MnO2 was used for the oxidation of 5 to give a mixture of the lactone 6 and lactol 7.The mixture can be reduced directly with a,n equivalant amount of diisobutylaluminum hydride to 7.The yield was comparable with that of the O2/Pt method.Compound 10 exhibits high luteolytic and antifertilitic effects with low smooth muscle spasmogenic activity.Further clinical trials are in progress.