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