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

Jordan C.T. Reddel, Kelly E. Lutz, Abdallah B. Diagne, Regan J. Thomson^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

35 Scopus citations

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.

Original language	English (US)
Pages (from-to)	1395-1398
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	5
DOIs	https://doi.org/10.1002/anie.201307659
State	Published - Jan 27 2014

Keywords

Cascade reactions
Hydrazones
Lignans
Natural product synthesis
Sigmatropic rearrangement

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201307659

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title = "Stereocontrolled syntheses of tetralone- and naphthyl-type lignans by a one-pot oxidative [3,3] rearrangement/friedel-crafts arylation",

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",

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AU - Reddel, Jordan C.T.

AU - Lutz, Kelly E.

AU - Diagne, Abdallah B.

AU - Thomson, Regan J.

PY - 2014/1/27

Y1 - 2014/1/27

N2 - 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.

AB - 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.

KW - Cascade reactions

KW - Hydrazones

KW - Lignans

KW - Natural product synthesis

KW - Sigmatropic rearrangement

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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