Roxbin B is cuspinin: Structural revision and total synthesis

Sayuri Yamaguchi, Tsukasa Hirokane, Takashi Yoshida, Takashi Tanaka, Tsutomu Hatano, Hideyuki Ito, Gen Ichiro Nonaka, Hidetoshi Yamada

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5410-5417
Number of pages8
JournalJournal of Organic Chemistry
Volume78
Issue number11
DOIs
Publication statusPublished - Jun 28 2013

ASJC Scopus subject areas

  • Organic Chemistry

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