Synthesis of (±)-6-protoilludene and (±)-3-EPI-6-protoilludene by intramolecular magnesium-ene- and ketene/alkene addition reactions

Von Oppolzer, Wolfgang; Nakao, Akio

doi:10.1016/S0040-4039(00)85240-5

Scientific article

English

Synthesis of (±)-6-protoilludene and (±)-3-EPI-6-protoilludene by intramolecular magnesium-ene- and ketene/alkene addition reactions

ContributorsVon Oppolzer, Wolfgang; Nakao, Akio

Published inTetrahedron letters, vol. 27, no. 45, p. 5471-5474

Publication date1986

Abstract

The sesquiterpene (±)-6-protoilludene (1) and its C(3)-epimer 11 were synthesized from aldehyde 5. The key steps are a regio- and stereo-selective type-I-magnesium-ene reaction 4 → 3 and an intramolecular vinylketene/alkene addition 2 → 9a + 9b. Synthesis of (±)-6-protoilludene (1) via Mg-ene reaction 4 → 3 and ketene-addition 2 →9.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, NAKAO, Akio. Synthesis of (±)-6-protoilludene and (±)-3-EPI-6-protoilludene by intramolecular magnesium-ene- and ketene/alkene addition reactions. In: Tetrahedron letters, 1986, vol. 27, n° 45, p. 5471–5474. doi: 10.1016/S0040-4039(00)85240-5

Article (Published version)

Identifiers

PID : unige:167202
DOI : 10.1016/S0040-4039(00)85240-5

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900852405

Journal ISSN0040-4039

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Synthesis of (±)-6-protoilludene and (±)-3-EPI-6-protoilludene by intramolecular magnesium-ene- and ketene/alkene addition reactions

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