C-Glycosidations Using Unprotected Sugars and Its Application to Synthesis of Bioactive Natural Products

Kazunobu Toshima, Goh Matsuo, Masaya Nakata, Shuichi Matsumura

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3 Citations (Scopus)

Abstract

Practical and highly stereo-selective aryl and allyl C-glycosidations using unprotected sugars as glycosyl donors have been developed. Aryl C-glycosidations of several unprotected 2-deoxy sugars with phenol and naphthol derivatives by the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf)-AgC104 or TMSOTf exclusively gave the corresponding unprotected o-hydroxyaryl β-C-glycosides which appear in many biologically attractive aryl C-glycoside antibiotics as the key subunit. On the other hand, allyl C-glycosidations of several unprotected glycals with allyltrimethylsilane by TMSOTf afforded the corresponding unprotected and 2,3-unsaturated allyl α-C-glycosides in high yields which are versatile synthetic intermediates for the syntheses of optically active natural products. Furthermore, the total synthesis of urdamycinone B, a prototypical member of the C-glycosyl angucycline antibiotics, was accomplished by the successful application of the present aryl C-glycosidation of unprotected sugar as the key step.

Original languageEnglish
Pages (from-to)841-850
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume56
Issue number10
DOIs
Publication statusPublished - 1998 Jan 1

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Keywords

  • 2,3-unsaturated allyl C-glycosides
  • Angucyclines
  • Aryl C-glycosides
  • C-Glycosyl juglone
  • C-glycosidation
  • Diels-Alder reaction
  • Photooxygenation
  • Trimethylsilyl trifluoromethanesulfonate
  • Unprotected sugar
  • Urdamycinone B

ASJC Scopus subject areas

  • Organic Chemistry

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