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Issue 0, 1974
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Plant proanthocyanidins. Part II. Proanthocyanidin-A2 and its derivatives

Abstract

The 2,7″-epoxy-4,8″-biflavan structure (1) has been deduced for the natural proanthocyanidin-A2 on the basis of spectroscopic (13C and 1H n.m.r.) and chemical evidence. Spectroscopic data are also outlined which lead, in association with biogenetic arguments, to a proposal (1a) for the absolute stereochemistry of the natural product. Hydrogenolysis of proanthocyanidin-A2 leads to fission of the C–O and C–C inter-flavan bonds and formation of the phenols (20) and (22). The same technique also leads to rupture of the inter-flavan linkage of dimers of the B group and hence to a novel micro-procedure for their identification. The isolation and characterisation of three trimeric proanthocyanidins based on A2 is also discussed.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1974, 2663-2671
Article type
Paper

Plant proanthocyanidins. Part II. Proanthocyanidin-A2 and its derivatives

D. Jacques, E. Haslam, G. R. Bedford and D. Greatbanks, J. Chem. Soc., Perkin Trans. 1, 1974, 2663
DOI: 10.1039/P19740002663

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