Synthesis of chiral prostanoid intermediates from phenol

Abstract

The 2-substituted derivatives of (4R)-4-hydroxycyclopent-2-enone (11) and (12), important intermediates in prostaglandin synthesis, are prepared from (4S)-3-chloro-4-(dimethyl-t-butylsilyloxy)cyclopent-2-enone (4) which is available in five steps from phenol.