TY - JOUR
T1 - Roxbin B is cuspinin
T2 - Structural revision and total synthesis
AU - Yamaguchi, Sayuri
AU - Hirokane, Tsukasa
AU - Yoshida, Takashi
AU - Tanaka, Takashi
AU - Hatano, Tsutomu
AU - Ito, Hideyuki
AU - Nonaka, Gen Ichiro
AU - Yamada, Hidetoshi
PY - 2013/6/28
Y1 - 2013/6/28
N2 - Prompted by the outcome that the synthesized roxbin B was not identical to the natural roxbin B, the structural determination process and spectral data were re-examined, with the finding that roxbin B was very likely to be 1-O-galloyl-2,3-(R);4,6-(S)-bis-O-hexahydroxydiphenoyl-β-d-glucose (cuspinin). Because the (R)-axial chirality is rare in natural products when the hexahydroxydiphenoyl group bridges the 2- and 3-oxygens, the proposed structure of cuspinin was confirmed by the total synthesis, leading to the conclusion that roxbin B is the same as cuspinin.
AB - Prompted by the outcome that the synthesized roxbin B was not identical to the natural roxbin B, the structural determination process and spectral data were re-examined, with the finding that roxbin B was very likely to be 1-O-galloyl-2,3-(R);4,6-(S)-bis-O-hexahydroxydiphenoyl-β-d-glucose (cuspinin). Because the (R)-axial chirality is rare in natural products when the hexahydroxydiphenoyl group bridges the 2- and 3-oxygens, the proposed structure of cuspinin was confirmed by the total synthesis, leading to the conclusion that roxbin B is the same as cuspinin.
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U2 - 10.1021/jo400562k
DO - 10.1021/jo400562k
M3 - Article
C2 - 23656490
AN - SCOPUS:84879284609
VL - 78
SP - 5410
EP - 5417
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 11
ER -