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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Communication
Synthesis of the Carbocyclic Core of Zoanthenol: Implementation of an Unusual Acid-Catalyzed Cyclization†
Article first published online: 19 APR 2007
DOI: 10.1002/anie.200700430
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Behenna, Douglas C., Stockdill, Jennifer L. and Stoltz, Brian M. (2007), Synthesis of the Carbocyclic Core of Zoanthenol: Implementation of an Unusual Acid-Catalyzed Cyclization. Angew. Chem. Int. Ed., 46: 4077–4080. doi: 10.1002/anie.200700430
- †
Publication History
- Issue published online: 16 MAY 2007
- Article first published online: 19 APR 2007
- Manuscript Received: 31 JAN 2007
Funded by
- Merck
- Pfizer
- Lilly
Keywords:
- alkaloids;
- asymmetric catalysis;
- cyclization;
- natural products
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.