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

doi:10.1021/jo400562k

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 journal › Article

14 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 language	English
Pages (from-to)	5410-5417
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	78
Issue number	11
DOIs	https://doi.org/10.1021/jo400562k
Publication status	Published - Jun 28 2013

ASJC Scopus subject areas

Organic Chemistry

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Yamaguchi, S., Hirokane, T., Yoshida, T., Tanaka, T., Hatano, T., Ito, H., Nonaka, G. I., & Yamada, H. (2013). Roxbin B is cuspinin: Structural revision and total synthesis. Journal of Organic Chemistry, 78(11), 5410-5417. https://doi.org/10.1021/jo400562k

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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.",

author = "Sayuri Yamaguchi and Tsukasa Hirokane and Takashi Yoshida and Takashi Tanaka and Tsutomu Hatano and Hideyuki Ito and Nonaka, {Gen Ichiro} and Hidetoshi Yamada",

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T1 - Roxbin B is cuspinin

T2 - Structural revision and total synthesis

AU - Yamaguchi, Sayuri

AU - Hirokane, Tsukasa

AU - Yoshida, Takashi

AU - Tanaka, Takashi

AU - Hatano, Tsutomu

AU - Ito, Hideyuki

AU - Nonaka, Gen Ichiro

AU - Yamada, Hidetoshi

PY - 2013/6/28

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AB - 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.

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