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Angew Chem Int Ed Engl. 2014 Jan 27;53(5):1395-8. doi: 10.1002/anie.201307659. Epub 2013 Dec 16.

Stereocontrolled syntheses of tetralone- and naphthyl-type lignans by a one-pot oxidative [3,3] rearrangement/Friedel-Crafts arylation.

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  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Rd, Evanston, IL 60208 (USA).

Abstract

The development of a stereoselective one-pot oxidative [3,3] sigmatropic rearrangement/Friedel-Crafts arylation that provides enantioenriched benzhydryl compounds is reported. The utility of this new transformation is demonstrated by the concise synthesis of several tetralone- and naphthyl-type lignan natural products, many of which display anti-malarial activity.

Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

cascade reactions; hydrazones; lignans; natural product synthesis; sigmatropic rearrangement

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