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

Abstract Attempted replacement of the allylic C 15 -acetate group in 9α,11α,15α-triacetoxycloprostenol 4-methoxybenzyl ester by tosyl group under phase-transfer conditions [CH 2 Cl 2 /H 2 O, R 3 R′N + Hlg – , NaOH, TsOH, Pd(PPh 3 ) 4 ] led to the formation of the corresponding (13 E ,15 Z ) 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(PPh 3 ) 4 and NaH.