An efficient synthesis of enantiomerically pure (1R,2S,5S)- and (1S,2R,5R)-rosaprostol methyl esters

摘要

We report a concise synthesis of the enantiomerically pure 1,2-trans-1,5-cis-methyl esters of rosaprostol, a prostaglandin derivative used for the treatment of gastric and duodenal ulcers, using as key step the chemo- and stereoselective Michael addition of a Grignard reagent to an unprotected hydroxycyclopentenone.