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Total synthesis of the triquinane marine sesquiterpene (±)Δ9(12)capnellene using a palladium-catalyzed bis-cyclization step.

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
50
Issue
2
Identifiers
DOI: 10.1016/s0040-4020(01)80763-8

Abstract

Abstract Details of a novel palladium catalyzed cyclization approach to linear condensed cyclopentanoids are reported. The mechanism of this reaction which involves a δ-ethylenic (or δ-acetylenic) carbon nucleophile and an unsaturated halide is a “Wacker type process” i.e, an attack by the nucleophile onto the unsaturation electrophilically activated by an organopalladium(II) species. In this paper, we will show the intramolocular version of this reaction which then leads to the tricyclic framework of the sesquiterpene (±)δ 9(12) capnellene, the total synthesis of which is described.

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