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A Tandem Cascade Cyclization−Electrophilic Aromatic Substitution: Application in the Total Synthesis of (+)-Angelichalcone

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Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294
[email protected]
Cite this: J. Am. Chem. Soc. 2009, 131, 41, 14630–14631
Publication Date (Web):September 25, 2009
https://doi.org/10.1021/ja906468v
Copyright © 2009 American Chemical Society
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    Abstract

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    When cascade cyclizations initiated by Lewis acid-mediated opening of an epoxide are terminated through reaction with a MOM-protected phenol, a tandem electrophilic aromatic substitution can be obtained. This highly regioselective tandem process has been employed in the first synthesis of (+)-angelichalcone.

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    Experimental details and the 1H and 13C NMR spectra for compounds 6−12, 16−18, 20−22, 24, and 25. This material is available free of charge via the Internet at http://pubs.acs.org.

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