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Asymmetric synthesis of (-)-incarvillateine employing an intramolecular alkylation via Rh-catalyzed olefinic C-H bond activation.

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.

SUBMITTER: Tsai AS

PROVIDER: S-EPMC2713182 | biostudies-literature | 2008 May

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of (-)-incarvillateine employing an intramolecular alkylation via Rh-catalyzed olefinic C-H bond activation.

Tsai Andy S AS Bergman Robert G RG Ellman Jonathan A JA

Journal of the American Chemical Society 20080429 20

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. ...[more]

PMID: 18444613

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