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Stereocontrolled total synthesis of the triquinane marine sesquiterpene Δ9(12)-capnellene

Leo A. Paquette, Kenneth E. Stevens


Canadian Journal of Chemistry, 1984, 62:(11) 2415-2420, 10.1139/v84-415

Abstract

A total synthesis of Δ9(12)-capnellene, a cis-anti-cis-tricyclo[6.3.0.02,6]undecane sesquiterpene of marine origin, is described. Starting with bicyclic enone 5, which was prepared by a Nazarov cyclization, the remaining portion of the molecule is elaborated by means of a new and relatively efficient cyclopentenone annulation scheme. The relative stereochemistries of the chiral centers are properly incorporated by taking advantage of prevailing steric factors.