(5Z,13E)-(15R)-16,16-dimethyl-9-oxo-15-(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid → (5Z,13E)-(15R)-16,16-Dimethyl-15-hydroxy-9-oxo-5,13-prostadien-18-ynoic Acid

Participants

Reaction Steps

At 20°, 390 mg. of (5Z,13E)-(15R)-16,16-dimethyl-9-oxo-15-(tetrahydropyran-2-yloxy)-5,13-prostadien-18-ynoic acid is agitated for 16 hours with 10 ml. of a mixture of glacial acetic acid/water/THF (65/35/10); the mixture is evaporated under vacuum and the residue purified by column chromatography on silica gel. With methylene chloride/5% methanol, 305 mg. of the title compound is obtained as a colorless oil.

Provenance & Evidence