Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan |
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Authors: | Oyama Kin-Ichi Kondo Tadao |
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Institution: | Chemical Instrument Center and Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan. |
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Abstract: | We succeeded in a first total synthesis of flavocommelin (1), a component of the blue supramolecular pigment, commelinin (2), from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 angstroms in CH2Cl2 and a catalytic amount of BF3 x Et2O. After 6-C-glycosylation of 4, oxidation with CAN to flavanone 18 and subsequent 4'-O-glycosylation, promoted with a combination of BF3 x Et2O and DTBMP, afforded diglucosylflavanone 20. DDQ oxidation of 20 and deprotection successively gave 1. |
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