Synthesis of aromatic modified prostaglandins from PGA2

Abstract

A general synthetic scheme, starting from PGA₂(obtained from the marine coral Plexaura homomalla), of prostaglandins modified in the upper chain is detailed. Key aldehyde intermediates have been secured from 11-deoxy-PGF_2α and PGF_2α by an efficient regioselective hydroxylation procedure followed by cleavage of the 5,6-double bond. Wittig reaction with these aldehydes provided the novel prostaglandins (5)–(8), belonging to the E and F families, and containing an aromatic ring in the upper chain.