Asymmetric Synthesis of (−)-Incarvillateine Employing an Intramolecular Alkylation via Rh-Catalyzed Olefinic C−H Bond Activation
- 29 April 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (20), 6316-6317
- https://doi.org/10.1021/ja8012159
Abstract
An asymmetric total synthesis of (−)-incarvillateine, a natural product having potent analgesic properties, has been achieved in 11 steps and 15.4% overall yield. The key step is a rhodium-catalyzed intramolecular alkylation of an olefinic C−H bond to set two stereocenters. Additionally, this transformation produces an exocyclic, tetrasubstituted alkene through which the bicyclic piperidine moiety can readily be accessed.Keywords
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