Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (±)??Ipalbidine
CW Jefford, T Kubota, A Zaslona
Index: Jefford, Charles W.; Kubota, Tadatoshi; Zaslona, Alexander Helvetica Chimica Acta, 1986 , vol. 69, p. 2048 - 2061
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Citation Number: 30
Abstract
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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