Journal
TETRAHEDRON
Volume 66, Issue 26, Pages 4668-4686Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.04.128
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Funding
- King Abdullah University of Science and Technology (KAUST) [KUS-11-006-02]
- NIH-NIGMS [R01 GM080269-01]
- Abbott
- Amgen
- Bristol-Myers Squibb
- Merck
- Caltech
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Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and alpha-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented. (C) 2010 Elsevier Ltd. All rights reserved.
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