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

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).

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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
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ISSN of the journal0018-019X
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