Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products

Joshua Fischer; Aaron J. Reynolds; Lisa A. Sharp; Michael S. Sherburn

doi:10.1021/ol049878b

Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products

Joshua Fischer
, Aaron J. Reynolds
, Lisa A. Sharp
, Michael S. Sherburn^*

^*Corresponding author for this work

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

85 Citations (SciVal)

Abstract

Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)α-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.

Original language	English
Pages (from-to)	1345-1348
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	9
DOIs	https://doi.org/10.1021/ol049878b
Publication status	Published - 29 Apr 2004

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title = "Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products",

abstract = "Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)α-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.",

author = "Joshua Fischer and Reynolds, \{Aaron J.\} and Sharp, \{Lisa A.\} and Sherburn, \{Michael S.\}",

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T1 - Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products

AU - Fischer, Joshua

AU - Reynolds, Aaron J.

AU - Sharp, Lisa A.

AU - Sherburn, Michael S.

PY - 2004/4/29

Y1 - 2004/4/29

N2 - Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)α-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.

AB - Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)α-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.

UR - https://www.scopus.com/pages/publications/2442630439

U2 - 10.1021/ol049878b

DO - 10.1021/ol049878b

M3 - Article

SN - 1523-7060

VL - 6

SP - 1345

EP - 1348

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products

Abstract

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