Abstract
The phenolic methyl ethers of flavan-3-ols, 4/gb-arylflavan-3-ols, and (−)-fisetinidol-(4β,8)-(+)-catechin biflavanoids are susceptible to regio- and stereoselective methoxylation at C-4 in moderate yields with DDQ in CHCl 3-MeOH solution. The observed asymmetric induction with exclusive formation of 2,4- trans products is compatible with the intermediacy of a diastereogenic donor-acceptor interaction, DDQ acting as the acceptor and oxidant. The 4-funtionalized analogues are of both synthetic and degradative significance in condensed tannin chemistry.
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