- An effective synthesis of isoorientin: The regioselective synthesis of a 6-C-glucosylflavone
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Isoorientin, a 6-C-β-D-glucopyranosyl-3',4',5,7-tetrahydroxyflavone, was synthesized in a 15% overall yield, in ten steps, starting from the commercially available phloroacetophenone. The C-glucosyl phloroacetophenone derivative, a synthetic intermediate that contains a free hydroxyl group that is para to the glucosyl moiety, was obtained by hydrogenolysis by taking advantage of differences in the hydrogenolysis rates between a benzyl protecting group and a 2-methylbenzyl protecting group. Aldol condensation of the C-glucosyl phloroacetophenone derivative with 3,4-bis-benzyloxybenzaldehyde afforded the corresponding chalcone as a precursor of the 6-C-glucosyl flavone. Construction of the flavone system by application of I2-DMSO, followed by deprotection, yielded isoorientin. (C) 2000 Elsevier Science Ltd.
- Kumazawa, Toshihiro,Minatogawa, Tomomi,Matsuba, Shigeru,Sato, Shingo,Onodera, Jun-Ichi
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p. 507 - 513
(2007/10/03)
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