Stereospecific (13)-thia-prostaglandin prepn. - from epoxide and thiol and giving prods. having (anti)prostaglandin activities

摘要

(A) The following process is new (i) R2-SH (III) or salt over right arrow (ii) deprotect if necessary (II) (or racemate, salt or ester) (I) (or racemate) (A = CO or CH(--OH); X = cis-vinylene or ethylene; B = 1-6C alkylene opt. substd. by one or more halogen, OH, 1-4C acyloxy or Ph gps.; R1 = 1-12C alkyl opt. substd. by one or more halogen, OH, 1-4C alkoxy, 1-4C acyloxy, Ph, OPh, pyridyl, thienyl or naphthyl gps., Ph or OPh substituents themselves being opt. substd. by Me, halogen, OH, OMe or halomethyl gps.; A1 = CO or CH(--OR); R = H or a protecting gp.; R2 is as R1 except that any OH gps. present may be protected). The product may be converted into salts or esters; X = vinylene may be catalytically hydrogenated to X = ethylene; obtd. racemates or diastereoisomeric mixts. may be resolved. (B) Intermediates (II; X = ethylene) are new.