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

DOI: 10.1002/hlca.19860690828

Source and publish data:

Helvetica Chimica Acta p. 2048 - 2061 (1986)

Update date:2022-07-29

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Authors:

Jefford, Charles W.

Kubota, Tadatoshi

Zaslona, Alexander

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Article abstract of DOI:10.1002/hlca.19860690828

A mew 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 82percent yield via an intramolecular carbenoid reaction.The latter compound was converted in four steps in 13percent overall yield to (+/-)-ipalbidine (1b).

Full text of DOI:10.1002/hlca.19860690828

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