jo400562k_si_001.pdf (4.92 MB)

Roxbin B is Cuspinin: Structural Revision and Total Synthesis

Download (4.92 MB)
journal contribution
posted on 07.06.2013, 00:00 by Sayuri Yamaguchi, Tsukasa Hirokane, Takashi Yoshida, Takashi Tanaka, Tsutomu Hatano, Hideyuki Ito, Gen-ichiro Nonaka, Hidetoshi Yamada
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.