Pd(PPh3)4-Catalyzed Elimination of Acetic Acid from (±)-9α,11α,15α-Triacetoxycloprostenol 4-Methoxybenzyl Ester

Abstract

Attempted replacement of the allylic C¹⁵-acetate group in 9α,11α,15α-triacetoxycloprostenol 4-methoxybenzyl ester by tosyl group under phase-transfer conditions [CH₂Cl₂/H₂O, R₃R′N⁺Hlg^–, NaOH, TsOH, Pd(PPh₃)₄] led to the formation of the corresponding (13E,15Z) derivative in a moderate yield as a result of elimination of acetic acid. The same product was obtained with high yield and stereoselectivity when the reaction was carried out in THF in the presence of Pd(PPh₃)₄ and NaH.