Total synthesis of (±)-Δ<sup>9(12)</sup>-capnellene via iterative intramolecular type-I-“Magnesium-ene” reactions

Von Oppolzer, Wolfgang; Bättig, Kurt

doi:10.1016/S0040-4039(00)85683-X

Scientific article

Letter

English

Total synthesis of (±)-Δ⁹⁽¹²⁾-capnellene via iterative intramolecular type-I-“Magnesium-ene” reactions

ContributorsVon Oppolzer, Wolfgang; Bättig, Kurt

Published inTetrahedron letters, vol. 23, no. 45, p. 4669-4672

Publication date1982

Abstract

The marine triquinane sesquiterpene Δ⁹(¹²)-capnellene (1) was synthesised from 2,2,5-trimethyl-5-hexenal (2) by a sequence of all synthetic operations in 5% overall yield. The key steps 3 → 4 → 5 → 6 involve two intramolecular type-I-“Mg-ene” processes.

Affiliation

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, BÄTTIG, Kurt. Total synthesis of (±)-Δ<sup>9(12)</sup>-capnellene via iterative intramolecular type-I-“Magnesium-ene” reactions. In: Tetrahedron letters, 1982, vol. 23, n° 45, p. 4669–4672. doi: 10.1016/S0040-4039(00)85683-X

Article (Published version)

Identifiers

PID : unige:168547
DOI : 10.1016/S0040-4039(00)85683-X

Commercial URLhttps://linkinghub.elsevier.com/retrieve/pii/S004040390085683X

ISSN of the journal0040-4039

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Total synthesis of (±)-Δ9(12)-capnellene via iterative intramolecular type-I-“Magnesium-ene” reactions

The marine triquinane sesquiterpene Δ9(12)-capnellene (1) was synthesised from 2,2,5-trimethyl-5-hexenal (2) by a sequence of all synthetic operations in 5% overall yield. The key steps 3 → 4 → 5 → 6 involve two intramolecular type-I-“Mg-ene” processes.

Technical informations

Total synthesis of (±)-Δ⁹⁽¹²⁾-capnellene via iterative intramolecular type-I-“Magnesium-ene” reactions

The marine triquinane sesquiterpene Δ⁹(¹²)-capnellene (1) was synthesised from 2,2,5-trimethyl-5-hexenal (2) by a sequence of all synthetic operations in 5% overall yield. The key steps 3 → 4 → 5 → 6 involve two intramolecular type-I-“Mg-ene” processes.