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

29 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)

Access to Document

10.1002/anie.201307659

Cite this

@article{3ea93168a4b748079f0e26e538ed5269,

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",

author = "Reddel, {Jordan C.T.} and Lutz, {Kelly E.} and Diagne, {Abdallah B.} and Thomson, {Regan J.}",

year = "2014",

month = jan,

day = "27",

doi = "10.1002/anie.201307659",

language = "English (US)",

volume = "53",

pages = "1395--1398",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "5",

}

Stereocontrolled syntheses of tetralone- and naphthyl-type lignans by a one-pot oxidative [3,3] rearrangement/friedel-crafts arylation. / Reddel, Jordan C.T.; Lutz, Kelly E.; Diagne, Abdallah B.; Thomson, Regan J.

In: Angewandte Chemie - International Edition, Vol. 53, No. 5, 27.01.2014, p. 1395-1398.

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

TY - JOUR

T1 - Stereocontrolled syntheses of tetralone- and naphthyl-type lignans by a one-pot oxidative [3,3] rearrangement/friedel-crafts arylation

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

UR - http://www.scopus.com/inward/record.url?scp=84893927074&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84893927074&partnerID=8YFLogxK

U2 - 10.1002/anie.201307659

DO - 10.1002/anie.201307659

M3 - Article

C2 - 24356917

AN - SCOPUS:84893927074

VL - 53

SP - 1395

EP - 1398

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 5

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

Access to Document

Other files and links

Fingerprint

Cite this