期刊名称：Proceedings of the National Academy of Sciences
印刷版ISSN：0027-8424
电子版ISSN：1091-6490
出版年度：1977
卷号：74
期号：6
页码：2199-2203
DOI：10.1073/pnas.74.6.2199
语种：English
出版社：The National Academy of Sciences of the United States of America
摘要：The structure of the most recently discovered, biologically highly active prostaglandin, PGI2 or prostacyclin, is correctly predicted on biogenetic grounds, and a general synthesis starting with prostaglandins of the F2alpha series is reported. Starting with the biologically active 13,14-dehydro-PGF2alpha, the synthesis involves formation of a 5-bromo-6,9alpha-epoxy derivative, followed by esterification and dehydrobromination of the methyl ester to form the prostacyclin structure. The stereochemistry at C-5 and C-6 of all reported products is assigned on the basis of experimental findings and mechanistic reasoning. 13,14-Dehydroprostacyclin methyl ester is considerably more stable at pH 7.5 than prostacyclin. It inhibits platelet aggregation induced by a variety of agents and causes an increase in renal blood flow in the dog at nanomolar levels.
