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Published May 25, 2007 | public
Journal Article

Synthesis of the Carbocyclic Core of Zoanthenol: Implementation of an Unusual Acid-Catalyzed Cyclization


A smokin' hot cyclization! When the racemic cyclization precursor is heated in neat trifluoroacetic acid, an unusual Friedel–Crafts-type cyclization forms the carbocyclic core of the marine alkaloid zoanthenol containing two all-carbon-substituted quaternary centers. Catalytic asymmetric alkylation allows entry into an enantioselective route.

Additional Information

© 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: January 31, 2007; Published online: April 19, 2007. The authors wish to thank the Fannie and John Hertz Foundation (predoctoral fellowship to D.C.B), Novartis (predoctoral fellowship to J.L.S.), Merck, Pfizer, and Lilly for financial support.

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