Asymmetric synthesis of a lignan lactone from a meso anhydride

• Published in: Tetrahedron Vol. 52; no. 39; pp. 12799 - 12814
• Main Authors: Ward, Robert S., Pelter, Andrew, Edwards, Mark I., Gilmore, Jeremy
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 23.09.1996; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; ENANTIOSELECTIVE REDUCTION; ACID; ALCOHOLYSIS

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