Stereoselective Synthesis of Flavonoids. Part 8. Free Phenolic Flavan-3-ol Diastereoisomers

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Reinier J. J. Nel, Hendrik van Rensburg, Pieter S. van Heerden and Daneel Ferreira


Abstract

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.


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