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

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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z700430_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.