Catalytic enantioselective total syntheses of bakkenolides I, J, and S: application of a carbene-catalyzed desymmetrization.
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.
Phillips
Eric M
EM
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Silverman Hall, Northwestern University, Evanston, Illinois 60208., USA.
Roberts
John M
JM
Scheidt
Karl A
KA
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D012717:Sesquiterpenes; C551666:bakkenolide I; C551667:bakkenolide J; C551668:bakkenolide S; C030011:carbene; D008697:Methane
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