American Chemical Society
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Thermal Elimination of Diethyldithiocarbamates and Application in the Synthesis of (±)-Ferrugine

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posted on 2008-10-17, 00:00 authored by Shamim Ahmed, Luke A. Baker, Richard S. Grainger, Paolo Innocenti, Camilo E. Quevedo
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 α,β- and/or β,γ-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.