Abstract
Oxidation of methyl
(E)-sinapate (1c) with 1 equiv. of ferric chloride in aqueous acetone gave the
tetralols (2a) and (2b), the dihydronaphthol(3a), and the lactone (4), all of
which result from C-C coupling, and an unidentified oil. The configurations of tetralols
(2a) and (2b) were ascertained by their conversion into (�)-lyoniresinol
dimethyl ether (5c) of known stereochemistry, and by p.m.r,
spectroscopy. The dimethyl ether (3b) of compound (3a) was identified as
thomasidioic acid dimethyl ether dimethyl ester. Reaction of phenol (1c) with
other one-electron oxidants is briefly discussed.
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32 articles.
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