Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (±)-Ipalbidine

Jefford, Charles; Kubota, Tadatoshi; Zaslona, Alexander Tadeusz

doi:10.1002/hlca.19860690828

Scientific article

English

Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (±)-Ipalbidine

ContributorsJefford, Charles; Kubota, Tadatoshi; Zaslona, Alexander Tadeusz

Published inHelvetica chimica acta, vol. 69, no. 8, p. 2048-2061

Publication date1986-12-10

First online date2004-10-25

Abstract

A new method for alkaloid synthesis is described. The rhodium(II)-acetate-catalyzed decomposition of 3-(4-acetoxyphenyl)-1-diazo-4-(pyrrol-1-yl)-2-butanone (5d) gave 6-(4-acetoxyphenyl)-5,6-dihydro-7(8H)-indolizinone (6d) in 82% yield via an intramolecular carbenoid reaction. The latter compound was converted in four steps in 13% overall yield to (±)-ipalbidine (1b).

Affiliation entities

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

Citation (ISO format)

JEFFORD, Charles, KUBOTA, Tadatoshi, ZASLONA, Alexander Tadeusz. Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (±)-Ipalbidine. In: Helvetica chimica acta, 1986, vol. 69, n° 8, p. 2048–2061. doi: 10.1002/hlca.19860690828

Article (Published version)

Identifiers

PID : unige:167147
DOI : 10.1002/hlca.19860690828

Commercial URLhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19860690828

Journal ISSN0018-019X

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Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (±)-Ipalbidine

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