Published May 25, 2007 | public
Journal Article

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

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Abstract

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.

Additional details

Created:
August 22, 2023
Modified:
October 24, 2023