Novel prostaglandin analogues and process for making same

Details Novel prostaglandin analogues and process for making same Novel prostaglandin analogues and process for making same

1982-05-05

1985-01-29

Gerstl, Robert

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

560121, C07C17700

Patent

active

044967594

ABSTRACT:
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 catalysts, 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-1-01-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.

REFERENCES:
patent: 4175201 (1979-11-01), Fried
patent: 4180672 (1979-12-01), Kurozumi et al.
Corey, "Studies on the Total Synthesis of Prostaglandins" Ann. N.Y. Acad. Sci. 180 (1971) 24.
Fried, et al. "Synthesis and Biological Activity of Prostaglandins and Prostaglandin Antagonists" Ann. N.Y. Acad. Sci., 180 (1971) 38.
Fried, et al. "Synthesis of (+) and (-)-7-Osaprostaglandin F.sub.1.alpha. and Their Epimers" J. Am. Chem. Soc. 93 (1971) 5593.
Fried et al., "Synthesis of (+)-7-oxaprostaglandin F.sub.1.alpha. ", Chem. Comm. (1968) 634.
Fried et al., "Regiospecific Epoxide Opening with Acetylenic Alanes" J. Am. Chem. Soc., 94 (1972) 4343.

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