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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 language | English |
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Pages (from-to) | 8116–8119 |
Number of pages | 4 |
Journal | The Journal of Organic Chemistry |
Volume | 73 |
Issue number | 20 |
Early online date | 12 Sept 2008 |
DOIs | |
Publication status | Published - 17 Oct 2008 |
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Dive into the research topics of 'Thermal elimination of diethyldithiocarbamates and application in the synthesis of (+/-)-ferrugine'. Together they form a unique fingerprint.Projects
- 1 Finished
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Harnessing Reactive Intermediates for Organic Synthesis
Engineering & Physical Science Research Council
1/10/05 → 31/03/09
Project: Research Councils