Short synthesis of isocarbacyclin by regioselective SN2′ alkylation of bicyclic allylic esters with zinc-copper reagents

Article abstract of DOI:10.1016/S0040-4020(01)96099-5

Isocarbacyclin [(+)-9(0)-methano-Δ^6(9α)-prostaglandin I₁] (2) was synthesized from bicyclic synthons such as 2-phosphorylated, 2-(thio)phosphorylated, 2-tosylated, 2-methoxycarbonylated, and 2-chloro-3-methylenebicyclo[3.3,0]octanes via highly regioselective S_N2′ alkylation with zinc-copper reagents 9 in excellent yields.