Roxbin B is Cuspinin: Structural Revision and Total Synthesis

Autor:	Sayuri Yamaguchi, Hideyuki Ito, Tsukasa Hirokane, Hidetoshi Yamada, Gen-Ichiro Nonaka, Takashi Yoshida, Takashi Tanaka, Tsutomu Hatano
Rok vydání:	2013
Předmět:	Biological Products Molecular Structure Stereochemistry Chemistry Organic Chemistry Molecular Conformation Total synthesis Spectral data Chirality (chemistry) Hydrolyzable Tannins
Zdroj:	The Journal of Organic Chemistry. 78:5410-5417
ISSN:	1520-6904 0022-3263
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5c7198cc64f65b67613b72f718f25e0e https://doi.org/10.1021/jo400562k Zobrazit plný text záznamu