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 |
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Rok vydání: | 2013 |
Předmět: | |
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 |
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