Thermal elimination of diethyldithiocarbamates and application in the synthesis of (+/-)-ferrugine

Shamim Ahmed, Luke A. Baker, Richard S. Grainger, Paolo Innocenti, Camilo E. Quevedo

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Dithiocarbamate-substituted lactams, prepared through group-transfer cyclization reactions of carbamoyl radicals, undergo a Chugaev-like thermal elimination of the dithiocarbamate group in refluxing diphenyl ether to form alpha,beta- and/or beta,gamma-unsaturated amides, depending on the structure of the starting material. This reaction sequence was used to prepare an unsaturated [3.2.2] bridged bicyclic amide, which was converted in a one-pot procedure to the 8-azabicyclo[3.2.1]octane ring system of the tropane alkaloid ferrugine by treatment with phenyllithium followed by aqueous sodium hydroxide.
Original languageEnglish
Pages (from-to)8116–8119
Number of pages4
JournalThe Journal of Organic Chemistry
Volume73
Issue number20
Early online date12 Sept 2008
DOIs
Publication statusPublished - 17 Oct 2008

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