C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/235.01, 204/
C07C 177/00 (1985.01)
Patent
CA 1221963
NOVEL PROSTAGLANDIN ANALOGUES AND PROCESS FOR MAKING SAME Edward David Mihelich ABSTRACT OF THE DISCLOSURE 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 1.DELTA.g state 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.
492580
Gowling Lafleur Henderson Llp
The Procter & Gamble Company
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