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Synthesis of Spiro C-Arylglycoriboside via Pd(II)-Catalyzed Spirocyclization

  作者 AWASAGUCHI KENICHIRO; MIYAZAWA MASAHIRO; UOYA IKUYO; INOUE KOICHI; NAKAMURA KOJI; YOKOYAMA HAJIME; KAKUDA HIROKO; HIRAI YOSHIRO  
  选自 期刊  SYNLETT;  卷期  2010年-16;  页码  2392-2396  
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[摘要]Spiro C-arylglycoriboside was synthesized in 21 steps via Pd(II)-catalyzed spirocyclization as a key reaction. Hemiketal was obtained in 47% overall yield from cis-2-butene-1,4-diol and spirocyclized with PdCl2(PhCN)(2) in dilute THF solution (0.01 M) to afford the 1,6-dioxaspiro[4.4] nonane skeleton in high yield. The spirocyclo adduct was transformed into spiro C-arylglycoriboside in five steps.

 
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