First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine

Tetrahedron Letters

Volumn 41, Issue 29, 2000, Pages 5537-5541

  Ohmori, Ken ^a   Ohrui, Hiroki ^a   Suzuki, Keisuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATECHIN; CHINESE DRUG; ETHER DERIVATIVE; FLAVAN DERIVATIVE; FLAVONOID; PLANT GLYCOSIDE; RHAMNOSE; SILVER CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHINESE MEDICINE; DRUG ACTIVITY; DRUG ISOLATION; DRUG SYNTHESIS; GLYCOSYLATION; NONHUMAN; OXIDATION; PLANT ROOT; TRADITIONAL MEDICINE;

EID: 0034661916     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00826-1     Document Type: Article

References (18)

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11. 3, 500 MHz) as shown below.
12. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
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15. 4, see: Matsumoto, T.; Hosoya, T.; Suzuki, K. Tetrahedron Lett. 1990, 31, 4629-4632.
16. 11 The conformations of the flavan skeleton in these compounds were deduced from the coupling constants. As for α-12, the conformation I was suggested, where two substituents at C(2) and C(3) were both equatorial. In contrast, surprisingly, the anomer β-12 adopts the conformation II, disposing the two substituents at axial positions.
17. The natural sample was kindly provided by Dr. Takashi Nakatsuka, Suntory.
18. 1H coupling constants, see: Bock, K.; Pedersen, C. J. Chem. Soc., Perkin Trans. 2 1974, 293-297.