Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 20, Pages 6316-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8012159
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Funding
- NIGMS NIH HHS [GM069559, R01 GM069559, R01 GM069559-05] Funding Source: Medline
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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 ran readily be accessed.
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