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

Jordan C T Reddel; Kelly E Lutz; Abdallah B Diagne; Regan J Thomson

doi:10.1002/anie.201307659

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

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

Authors

Jordan C T Reddel¹, Kelly E Lutz, Abdallah B Diagne, Regan J Thomson

Affiliation

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

PMID: 24356917
DOI: 10.1002/anie.201307659

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.

Keywords: cascade reactions; hydrazones; lignans; natural product synthesis; sigmatropic rearrangement.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Antimalarials / chemical synthesis
Antimalarials / chemistry
Hydrazones / chemistry
Lignans / chemical synthesis*
Lignans / chemistry
Oxidation-Reduction
Stereoisomerism
Tetralones / chemistry*

Substances

Antimalarials
Hydrazones
Lignans
Tetralones
pycnanthulignene B