Asymmetric dihydroxylation of a series of poly-O-methoxymethyl-1,3-diarylpropenes with AD-mix-α or AD-mix-β and subsequent acid-catalyzed cyclization of the intermediate syn-diols permits the first synthetic access to all four diastereoisomers of free phenolic flavan-3-ols in high enantiomeric excess and yield.
R. J. J. Nel, H. van Rensburg, P. S. van Heerden and D. Ferreira, J. Chem. Res. (S), 1999, 606 DOI: 10.1039/A904499J
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