Synthesis of (±)-hirsutene by a catalytic allylpalladium-alkyne cyclization/carbonylation cascade

Von Oppolzer, Wolfgang; Robyr, Chantal

doi:10.1016/S0040-4020(01)80764-X

Scientific article

English

Synthesis of (±)-hirsutene by a catalytic allylpalladium-alkyne cyclization/carbonylation cascade

ContributorsVon Oppolzer, Wolfgang; Robyr, Chantal

Published inTetrahedron, vol. 50, no. 2, p. 415-424

Publication date1994

Abstract

The tricyclic terpenoid (±)-hirsutene (1) has been synthesized starting from 2-hydroxy-4,4-dimethyltetrahydropyrane (8). In the key step, acyclic enynyl carbonate 7 afforded bicyclooctenone 2 via a 85% diastereoselective palladium catalyzed metallo-ene/carbonylation reaction cascade. The third ring was closed by a radical/alkene addition 19 → 20.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, ROBYR, Chantal. Synthesis of (±)-hirsutene by a catalytic allylpalladium-alkyne cyclization/carbonylation cascade. In: Tetrahedron, 1994, vol. 50, n° 2, p. 415–424. doi: 10.1016/S0040-4020(01)80764-X

Article (Published version)

Identifiers

PID : unige:151911
DOI : 10.1016/S0040-4020(01)80764-X

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S004040200180764X

Journal ISSN0040-4020

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Synthesis of (±)-hirsutene by a catalytic allylpalladium-alkyne cyclization/carbonylation cascade

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