Stereoselective total syntheses of (±)-sinularene and of (±)-5-epi-sinularene via intramolecular type-I-“magnesium-ene” reaction

Von Oppolzer, Wolfgang; Strauss, Heinrich F.; Simmons, Dana Philip

doi:10.1016/S0040-4039(00)85684-1

Scientific article

Letter

English

Stereoselective total syntheses of (±)-sinularene and of (±)-5-epi-sinularene via intramolecular type-I-“magnesium-ene” reaction

ContributorsVon Oppolzer, Wolfgang; Strauss, Heinrich F.; Simmons, Dana Philip

Published inTetrahedron letters, vol. 23, no. 45, p. 4673-4676

Publication date1982

Abstract

(±)-Sinularene (1) as well as (±)-5-epi-sinularene (9) were synthesised in a stereocontrolled manner from the norbornene 2 in overall yields of 4% and 8%, respectively. The key step 5 → 6 involves a regio- and stereoselective intramolecular “magnesium-ene” reaction.

Affiliation

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, STRAUSS, Heinrich F., SIMMONS, Dana Philip. Stereoselective total syntheses of (±)-sinularene and of (±)-5-epi-sinularene via intramolecular type-I-“magnesium-ene” reaction. In: Tetrahedron letters, 1982, vol. 23, n° 45, p. 4673–4676. doi: 10.1016/S0040-4039(00)85684-1

Article (Published version)

Identifiers

PID : unige:168546
DOI : 10.1016/S0040-4039(00)85684-1

Commercial URLhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900856841

ISSN of the journal0040-4039

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Stereoselective total syntheses of (±)-sinularene and of (±)-5-epi-sinularene via intramolecular type-I-“magnesium-ene” reaction

(±)-Sinularene (1) as well as (±)-5-epi-sinularene (9) were synthesised in a stereocontrolled manner from the norbornene 2 in overall yields of 4% and 8%, respectively. The key step 5 → 6 involves a regio- and stereoselective intramolecular “magnesium-ene” reaction.

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