(+/-)-(5Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-(tetrahydropyran-2-yloxy)-cyclopentyl}-5-heptenic acid methyl ester → (+/-)-(Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-hydroxy-cyclopentyl}-5-heptenic acid methyl ester heptenic acid methyl ester

Participants

Reaction Steps

1 g of VIII is stirred for 24 hours at 40° C. with 25 ml of a mixture of glacial acetic acid-water-tetrahydrofuran (65/35/10). It is concentrated by evaporation in a vacuum, chromatographed on silica gel with hexane/10-50% ethyl acetate, and 720 mg of IX is obtained as oil.

Provenance & Evidence