A Short Asymmetric Synthesis of (+)-Lyoniresinol Dimethyl Ether

A short, efficient synthesis of the lignan (+)-lyoniresinol dimethyl ether is described. The synthesis is achieved by asymmetric photocyclization of an achiral dibenzylidenesuccinate to a chiral aryldihydronaphthalene. (−)-Ephedrine is used as a chiral auxiliary to bias the atropisomeric equilibrium...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2004-06, Vol.69 (12), p.4140-4144
Main Authors: Assoumatine, Tokouré, Datta, Probal K, Hooper, Timothy S, Yvon, Brigitte L, Charlton, James L
Format: Article
Language:English
Subjects:
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
General and physical chemistry
Organic chemistry
Photochemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A short, efficient synthesis of the lignan (+)-lyoniresinol dimethyl ether is described. The synthesis is achieved by asymmetric photocyclization of an achiral dibenzylidenesuccinate to a chiral aryldihydronaphthalene. (−)-Ephedrine is used as a chiral auxiliary to bias the atropisomeric equilibrium in the dibenzylidenesuccinate prior to the photochemical reaction. The synthesis of the title compound was accomplished in five steps, and the final product was recrystallized to constant melting point and rotation.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0497454