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Synlett 1991; 1991(10): 709-711
DOI: 10.1055/s-1991-34769
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O → C-Glycoside Rearrangement of Resorcinol Derivatives. Versatile Intermediates in the Synthesis of Aryl C-Glycosides

Takashi Matsumoto* , Takamitsu Hosoya, Keisuke Suzuki
  • *Department of Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223, Japan
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Publication Date:
13 March 2002 (online)

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C-Glycoside formation of mono-protected resorcinols is described. Treatment of mono-O-acyl resorcinols with glycosyl fluoride 1 (2,3,5-tri-O-methyl-α-D-ribofuranosyl fluoride) at -78 °C in the presence of diethyl ether-boron trifluoride or hafnocene dichloride/silver perchlorate led to rapid formation of the O-aryl glycoside. Subsequent warming of the reaction mixture effected conversion of the O-glycoside to the corresponding C-glycoside. The aryl C-glycoside bond was selectively formed at the ortho-position of the free phenolic hydroxyl group. Several selective manipulations of the products are described, which clearly illustrate their versatility as synthetic intermediates for natural aryl C-glycoside antibiotics.

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