Roxbin B is Cuspinin: Structural Revision and Total Synthesis

详细信息    查看全文

• 作者：Sayuri Yamaguchi ; Tsukasa Hirokane ; Takashi Yoshida ; Takashi Tanaka ; Tsutomu Hatano ; Hideyuki Ito ; Gen-ichiro Nonaka ; Hidetoshi Yamada
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：June 7, 2013
• 年：2013
• 卷：78
• 期：11
• 页码：5410-5417
• 全文大小：463K
• 年卷期：v.78,no.11(June 7, 2013)
• ISSN：1520-6904

文摘

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-尾-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.