Catalytic enantioselective total syntheses of bakkenolides I, J, and S: application of a carbene-catalyzed desymmetrization.

ABSTRACT: A general strategy for the catalytic asymmetric syntheses of the bakkenolides is reported. The key bond-forming step involves an N-heterocyclic carbene catalyzed desymmetrization of a 1,3-diketone to form three new bonds in one step with excellent enantio- and diastereoselectivity. This intramolecular reaction allows direct access to the hydrindane core of the bakkenolide family and enables a facile synthesis of these natural products.

SUBMITTER: Phillips EM 

PROVIDER: S-EPMC2884059 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature