title: Roxbin B is cuspinin: structural revision and total synthesis.
abstract: 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.
authors: School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan.
authors: Sayuri
authors: S
authors: Yamaguchi
authors: Tsukasa
authors: T
authors: Hirokane
authors: Takashi
authors: T
authors: Yoshida
authors: Takashi
authors: T
authors: Tanaka
authors: Tsutomu
authors: T
authors: Hatano
authors: Hideyuki
authors: H
authors: Ito
authors: Gen-ichiro
authors: G
authors: Nonaka
authors: Hidetoshi
authors: H
authors: Yamada
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D047348:Hydrolyzable Tannins / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure
chemical_list: D001688:Biological Products; D047348:Hydrolyzable Tannins; C053931:roxbin B