A Model for the Elaboration of the (S)-3-Hydroxy-trans-1-Octenyl Side Chain of Prostanoids

Any synthetic route to prostaglandins depends in part on the availability of a method for stereospecific elaboration of the (S)-3-hydroxytrans-1-octenyl side chain (cf. PGE1)1. This communication presents an approach to this problem which has been developed by appropriate modification of the recently reported process for the synthesis of acetylenes (eq 1–3)2,3. We report here the conversion of cyclopentene into the vinyl cyclopentane 4 possessing the (S)-3-hydroxy-trans-1-octenyl side chain (see Scheme).