Preparation of a Key Intermediate for the Synthesis of the (±)-Pentalenolactone E Methyl Ester by Catalytic 'Palladium-Ene Cyclization'/Methoxycarbonylation

Von Oppolzer, Wolfgang; Xu, Jin-Zhu; Stone, Charles

doi:10.1002/hlca.19910740302

Scientific article

English

Preparation of a Key Intermediate for the Synthesis of the (±)-Pentalenolactone E Methyl Ester by Catalytic 'Palladium-Ene Cyclization'/Methoxycarbonylation

ContributorsVon Oppolzer, Wolfgang; Xu, Jin-Zhu; Stone, Charles

Published inHelvetica Chimica Acta, vol. 74, no. 3, p. 465-468

Publication date1991

Abstract

Bicyclic alcohol (±)-2, an advanced intermediate for the synthesis of the methyl ester 1 of pentalenolactone E, has been synthesized in nine operations starting from aldehyde 7. The key step 6 → 9 is a Pd-catalyzed, tandem intramolecular alkyne allylation/carbonylation reaction.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, XU, Jin-Zhu, STONE, Charles. Preparation of a Key Intermediate for the Synthesis of the (±)-Pentalenolactone E Methyl Ester by Catalytic “Palladium-Ene Cyclization”/Methoxycarbonylation. In: Helvetica Chimica Acta, 1991, vol. 74, n° 3, p. 465–468. doi: 10.1002/hlca.19910740302

Article (Published version)

Identifiers

PID : unige:152517
DOI : 10.1002/hlca.19910740302

Additional URL for this publicationhttp://doi.wiley.com/10.1002/hlca.19910740302

Journal ISSN0018-019X

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Preparation of a Key Intermediate for the Synthesis of the (±)-Pentalenolactone E Methyl Ester by Catalytic 'Palladium-Ene Cyclization'/Methoxycarbonylation

Bicyclic alcohol (±)-2, an advanced intermediate for the synthesis of the methyl ester 1 of pentalenolactone E, has been synthesized in nine operations starting from aldehyde 7. The key step 6 → 9 is a Pd-catalyzed, tandem intramolecular alkyne allylation/carbonylation reaction.

Technical informations