Acta Chimica Sinica ›› 1980, Vol. 38 ›› Issue (4): 371-376.
褚季瑜1, 鲁秀英1, 方雪君1, 阮尚冏2, 李志源2
CHU JI-YU1, LU XIU-YING1, FANG XUE-JUN1, RUAN SHANG-JIONG2, LI ZHI-YUAN2
A new prostaglandin analog 15(R, S)-dl-ω-ethyl-13, 14-dehydro-prostaglandin F2α (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.
CHU JI-YU, LU XIU-YING, FANG XUE-JUN, RUAN SHANG-JIONG, LI ZHI-YUAN. SYNTHESIS OF 15(R, S)-dl-ω-ETHYL-13, 14-DEHYDRO PROSTAGLANDIN F2α[J]. Acta Chimica Sinica, 1980, 38(4): 371-376.
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