Naturally occurring optically active flavans

Tetrahedron Letters
1970.0

Abstract

From the benzene extracts of two species of Dianellinae have been isolated two optically active flavans. We believe this to be the first report of the isolation of a natural flavan possessing optical activity, and indeed one of the few reports of a natural flavan not containing an oxygen atom attached to the heterocyclic ring. Previous examples are racemic 4',5,7-trimethoxyflavan, isolated from a methylated extract of a Xanthorrhoea, and 4'-methoxyflavan, isolated from the scent glands of the Canadian beaver (Castor fiber)2. We wish to report the isolation from Stypandra grandis of (-)-4'-hydroxy-7-methoxyflavan (I), and from Dianella revoluta of (-)-4'-hydroxy-7-methoxy-8-methylflavan (II).

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