Application of the intramolecular magnesium-ene reaction to the stereocontrolled total syntheses of (±)-12-acetoxysinularene and (±)-5-epi-12-acetoxysinularene

Von Oppolzer, Wolfgang; Begley, Tadhg; Ashcroft, Alison Elisabeth

doi:10.1016/S0040-4039(01)80037-X

Scientific article

Letter

English

Application of the intramolecular magnesium-ene reaction to the stereocontrolled total syntheses of (±)-12-acetoxysinularene and (±)-5-epi-12-acetoxysinularene

ContributorsVon Oppolzer, Wolfgang; Begley, Tadhg; Ashcroft, Alison Elisabeth

Published inTetrahedron letters, vol. 25, no. 8, p. 825-828

Publication date1984

Abstract

The sesquiterpene (±)-12-acetoxysinularene (1) and its C(5)-epimer (13) were each synthesized stereoselectively from the norbornyl-iodoacetal 7 in 5% and 7% overall yields. The critical step (10) → (11) involves the regio- and stereoselective “magnesium-ene” reaction (6) → (5).

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, BEGLEY, Tadhg, ASHCROFT, Alison Elisabeth. Application of the intramolecular magnesium-ene reaction to the stereocontrolled total syntheses of (±)-12-acetoxysinularene and (±)-5-epi-12-acetoxysinularene. In: Tetrahedron letters, 1984, vol. 25, n° 8, p. 825–828. doi: 10.1016/S0040-4039(01)80037-X

Article (Published version)

Identifiers

PID : unige:168000
DOI : 10.1016/S0040-4039(01)80037-X

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S004040390180037X

Journal ISSN0040-4039

79views

0downloads

Creation04/05/2023 9:12:37 AM

First validation04/05/2023 9:55:30 AM

Update time04/05/2023 9:55:30 AM

Status update04/05/2023 9:55:30 AM

Last indexation11/01/2024 4:42:54 AM

Archive ouverte UNIGE

Application of the intramolecular magnesium-ene reaction to the stereocontrolled total syntheses of (±)-12-acetoxysinularene and (±)-5-epi-12-acetoxysinularene

The sesquiterpene (±)-12-acetoxysinularene (1) and its C(5)-epimer (13) were each synthesized stereoselectively from the norbornyl-iodoacetal 7 in 5% and 7% overall yields. The critical step (10) → (11) involves the regio- and stereoselective “magnesium-ene” reaction (6) → (5).

Technical informations