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

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

doi:10.1021/ja906468v

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Journal article

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

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

Journal of the American Chemical Society, Vol.131(41), pp.14630-14631

10/21/2009

DOI: 10.1021/ja906468v

PMID: 19824722

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Abstract

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.

Xanthenes - chemical synthesis

Chalcone - chemistry

Chalcone - analogs & derivatives

Cyclization

Stereoisomerism

Xanthenes - chemistry

Substrate Specificity

Chalcone - chemical synthesis

Details

Title: Subtitle: A tandem cascade cyclization-electrophilic aromatic substitution: application in the total synthesis of (+)-angelichalcone
Creators: Joseph J Topczewski - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USA
Michael P Callahan
Jeffrey D Neighbors
David F Wiemer
Resource Type: Journal article
Publication Details: Journal of the American Chemical Society, Vol.131(41), pp.14630-14631
DOI: 10.1021/ja906468v
PMID: 19824722
NLM abbreviation: J Am Chem Soc
ISSN: 0002-7863
eISSN: 1520-5126
Publisher: United States
Language: English
Date published: 10/21/2009
Academic Unit: Neuroscience and Pharmacology; Chemistry
Record Identifier: 9983986000102771

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