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.
Journal article
2008-10-01T00:00:00+00:00
73
8116 - 8119
3
School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.
Lactams, Ditiocarb, Temperature, Cyclization, Stereoisomerism, Bridged Bicyclo Compounds, Heterocyclic