A tandem cascade cyclization-electrophilic aromatic substitution: Application in the total synthesis of (+)-angelichalcone

Joseph J. Topczewski; Michael P. Callahan; Jeffrey Neighbors; David F. Wiemer

doi:10.1021/ja906468v

A tandem cascade cyclization-electrophilic aromatic substitution: Application in the total synthesis of (+)-angelichalcone

Joseph J. Topczewski, Michael P. Callahan, Jeffrey Neighbors, David F. Wiemer

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Abstract

(Chemical Equation Presented) 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.

Original language	English (US)
Pages (from-to)	14630-14631
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	41
DOIs	https://doi.org/10.1021/ja906468v
State	Published - Oct 21 2009

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja906468v

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title = "A tandem cascade cyclization-electrophilic aromatic substitution: Application in the total synthesis of (+)-angelichalcone",

abstract = "(Chemical Equation Presented) 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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AU - Topczewski, Joseph J.

AU - Callahan, Michael P.

AU - Neighbors, Jeffrey

AU - Wiemer, David F.

PY - 2009/10/21

Y1 - 2009/10/21

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

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A tandem cascade cyclization-electrophilic aromatic substitution: Application in the total synthesis of (+)-angelichalcone

Abstract

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