Asymmetric synthesis of a lignan lactone from a meso anhydride

The synthesis of a meso-2,3-dibenzylbutanedioic acid anhydride is given. Reaction of this with (+)-α-methylbenzylamine proceeds diastereoselectively to give a butanedioic acid monoamide which is converted into an enantiomerically enriched cis-2,3-dibenzylbutyrolactone lignan. Graphic

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 52; no. 39; pp. 12799 - 12814
Main Authors Ward, Robert S., Pelter, Andrew, Edwards, Mark I., Gilmore, Jeremy
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.09.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENANTIOSELECTIVE REDUCTION
ACID
ALCOHOLYSIS
Online AccessGet full text

Cover

More Information
Summary:The synthesis of a meso-2,3-dibenzylbutanedioic acid anhydride is given. Reaction of this with (+)-α-methylbenzylamine proceeds diastereoselectively to give a butanedioic acid monoamide which is converted into an enantiomerically enriched cis-2,3-dibenzylbutyrolactone lignan. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00761-2