Synthesis of flavan-3, 4-diols, stereochemistry of novel biflavanols and new non-tannins from Acacia Mearnsii

Abstract

From Summary: The structural elucidation of condensed tannins, which are considered to consist of Câ‚ â‚…-flavan units, presents certain difficulties. These tannins occur in extremely complex mixtures, and their isolation is complicated by their susceptibility to oxidative denaturation. Limitations in the formation of significant degradation products add to these problems. Since condensed tannins of black wattle bark yield anthocyanidins on treatment with mineral acids, they are considered to be proanthocyanidin in character. For this reason the initial approach to the investigation of the structures of condensed tannins was by way of the synthesis of novel 7-hydroxyflavan-3,4-diols having a low degree of hydroxyl substitution. Submission of these to modern physical techniques such as nuclear magnetic resonance (n.m.r.) spectroscopy would yield valuable data regarding the chemical shifts and coupling constants of heterocyclic and benzenoid protons which may be used for subsequent work on more highly hydroxylated diols, biflavanols and finally the condensed tannins themselves.