Journal
TETRAHEDRON
Volume 68, Issue 29, Pages 5759-5778Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.05.037
Keywords
Delphinium alkaloids; azabicyclo[3.3.1]nonanes; Mannich reaction; Diels-Alder reaction
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Funding
- University of Auckland
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The one-pot TiCl4 catalysed Diels-Alder/Mannich reaction of alpha-cyanoaminoacrylates with 2-silyloxy-1,4-butadienes gives 6-keto-3-azabicyclo[3.3.1]nonane-1-carboxylates. Reduction of the ketone and alkylation of the resultant alcohol gives 6-alkoxy-3-azabicyclo[3.3.1]nonanes mimicking the AE rings of a number of Delphinium and Aconitum alkaloids, with the same stereochemistry as the natural products. (C) 2012 Elsevier Ltd. All rights reserved.
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