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Synlett 2020; 31(14): 1389-1393
DOI: 10.1055/s-0040-1707812
letter
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Phyllanemblinin B

Shintaro Matsumoto 
a   School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan   Email: shinnosuke1010@kwansei.ac.jp
,
Shinnosuke Wakamori  ∗
a   School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan   Email: shinnosuke1010@kwansei.ac.jp
,
Kentaro Nishii
a   School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan   Email: shinnosuke1010@kwansei.ac.jp
,
Takashi Tanaka
b   Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan
,
Hidetoshi Yamada 
a   School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan   Email: shinnosuke1010@kwansei.ac.jp
› Author AffiliationsJapan Society for the Promotion of Science (JP16H01163, JP18H04429)
Further Information

Publication History

Received: 05 April 2020

Accepted after revision: 26 April 2020

Publication Date:
10 June 2020 (online)

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◊ These authors contributed equally to this work.

Abstract

A total synthesis was developed of phyllanemblinin B, a natural ellagitannin containing 1-O-galloyl and 2,4-O-hexahydroxydiphenoyl groups on a d-glucose scaffold. The use of a μ-hydroxo copper(II) complex resulted in a completely stereoselective oxidative coupling of the galloyl groups on the open-chain glucose moiety and facilitated the first total synthesis of phyllanemblinin B.

Key words

total synthesis - natural products - ellagitannins - phyllanemblinin B - oxidative coupling

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707812.
  • Supporting Information
 

  • References and Notes

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