88607-74-3Relevant articles and documents
Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan
Oyama, Kin-Ichi,Kondo, Tadao
, p. 5240 - 5246 (2007/10/03)
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 A in CH2Cl2 and a catalytic amount of BF3·Et2O. After 6-C-glycosylation of 4, oxidation with CAN to flavanone 18 and subsequent 4′-O-glycosylation, promoted with a combination of BF3·Et2O and DTBMP, afforded diglucosylflavanone 20. DDQ oxidation of 20 and deprotection successively gave 1.