Thermal Elimination of Diethyldithiocarbamates and Application in the Synthesis of (?-Ferrugine.

[摘要]：cyclization reactions of carbamoyl radicals, undergo a Chugaev-like thermal elimination of the dithiocarbamate group in refluxing di-Ph ether to form a,b- and/or b,g-unsatd. amides, depending on the structure of the starting material. This reaction sequence was used to prep. an unsatd. [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 (I) by treatment with phenyllithium followed by aq. sodium hydroxide.

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