Synthesis of 15-cis-(4-n-Propylcyclohexyl)-16, 17, 18, 19, 20-pentanor-9-deoxy-6, 9α-nitriloprostaglandin F₁ Methyl Ester (OP-2507), a Novel Anti-cerebral Ischemic Agent

Abstract

Synthesized was 15-cis-(4-n-propylcyclohexyl)-16, 17, 18, 19, 20-pentanor-9-deoxy-6, 9α-nitrilo-prostaglandin F₁ methyl ester (OP-2507), a novel, promising anti-cerebral ischemic agent. A key intermediate, methyl cis-4-n-propylcyclohexanecarboxylate, was prepared stereoselectively by the hydrogenation of methyl 4-n-propylbenzoate with commercially available dimer of chloro(1, 5-cyclooctadiene)rhodium as a catalyst. Stereoselective reduction of C₁₅-ketone to C_15α-alcohol was achieved with diisobutylaluminum 2, 6-di-tert-butyl-4-methylphenoxide.