Prostanoids: XC. Extension to the synthesis of enprostil of the o-nitrophenylsulfonylhydrazine method for transformation of 2-propynyl alcohols into allenes

Abstract

A potential precursor of enprostil, (±)-9-acetoxy-11,15-di-O-(tert- butyldimethylsilyl)-2-decarboxy-6-hydroxy-16-phenoxy-2-triphenylmethyloxymethyl- 4,4,5,5-tetradehydro-17,18,19,20-tetranorprostaglandin F1α, was synthesized. This compound remained unchanged under the conditions for generation of allenes from 2-propynyl alcohols by the action of the system diisopropyl azodicarboxylate-triphenylphosphine-o-nitrophenylsulfonylhydrazine. © 2005 Pleiades Publishing, Inc.