A total synthesis of (±)-isocomene and (±) <i>β</i>-isocomene by an intramolecular ene reaction

Von Oppolzer, Wolfgang; Bättig, Kurt; Hudlicky, Thomas

doi:10.1016/0040-4020(81)80001-4

Scientific article

English

A total synthesis of (±)-isocomene and (±) β-isocomene by an intramolecular ene reaction

ContributorsVon Oppolzer, Wolfgang; Bättig, Kurt; Hudlicky, Thomas

Published inTetrahedron, vol. 37, no. 25, p. 4359-4364

Publication date1981

Abstract

The racemic sesquiterpenes isocomene 1 and β-isocomene 22 have been synthesized starting from 1,7-octadien-3-one 10 in a stereoselective manner. In the key step 12 → 13 (Scheme 5) the C-7, C-8-bond was formed by an intramolecular thermal ene reaction. Further transformations of 13 (Scheme 6) involved successively ring contraction 18 → 19, elimination 21 → 22 and olefin isomerization 22 → 1.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, BÄTTIG, Kurt, HUDLICKY, Thomas. A total synthesis of (±)-isocomene and (±) β-isocomene by an intramolecular ene reaction. In: Tetrahedron, 1981, vol. 37, n° 25, p. 4359–4364. doi: 10.1016/0040-4020(81)80001-4

Article (Published version)

Identifiers

PID : unige:169218
DOI : 10.1016/0040-4020(81)80001-4

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/0040402081800014

Journal ISSN0040-4020

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A total synthesis of (±)-isocomene and (±) β-isocomene by an intramolecular ene reaction

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