CONVERSION OF OLEFINS TO ALPHA EPOXY ALCOHOLS; PREPARATION OF PROSTAGLANDINS; 7-OXA-11-DEOXY PROSTAGLANDINS

摘要

A novel process for the oxidation of olefins to the corresponding alpha-epoxy alcohols which can be incorporated in the total synthesis of members of a novel class of prostaglandin analogues. Olefins are reacted with singlet oxygen in the presence of a group IVB, VB or VIB transition metal catalyst, excluding chromium. The reaction is fast and highly selective to the alpha-epoxy alcohol. When cyclopentene is oxidized in the process of the invention, high yields of cis 2,3-epoxy-cyclopentan-1-ol are obtained. The latter compound is used as a starting material in the synthesis of prostaglandin analogues. The prostanoids of the invention are characterized by an oxa group replacing the methylene group at the 7-position, and the absence of a hydroxyl or other substituent at the 11-position. Members of this class of prostanoids show important cytoprotective properties in animal tests.