- Simple synthesis of sakuranetin and selinone via a common intermediate, utilizing complementary regioselectivity in the deacetylation of naringenin triacetate
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Sakuranetin and selinone were successfully synthesized utilizing the regioselective deacetylation of naringenin triacetate. Deacetylation of the latter at C-7 with imidazole in 1,4-dioxane at 40°C furnished the corresponding diacetate in 80% yield. Methyl
- Yamashita, Yasunobu,Hanaya, Kengo,Shoji, Mitsuru,Sugai, Takeshi
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- 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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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.
- Oyama, Kin-Ichi,Kondo, Tadao
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p. 5240 - 5246
(2007/10/03)
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