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Synlett 2010(16): 2392-2396  
DOI: 10.1055/s-0030-1258560
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Ken-ichiro Awasaguchia, Masahiro Miyazawa*b, Ikuyo Uoyab, Koichi Inoueb, Koji Nakamurab, Hajime Yokoyamab, Hiroko Kakudac, Yoshiro Hirai*a
a Graduate School of Innovative Life Science, University of Toyama, 3190 Gohuku, Toyama 930-8555, Japan
Fax: +81(764)456115; e-Mail: hirai@adm.u-toyama.ac.jp;
b Faculty of Science, Department of Chemistry, University of Toyama, 3190 Gohuku, Toyama 930-8555, Japan
e-Mail: miyazawa@sci.toyama-u.ac.jp;
c Faculty of Medicine, Laboratory of Chemistry, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
Further Information

Publication History

Received 10 June 2010
Publication Date:
03 September 2010 (online)

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Abstract

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.

Key words

spiro compound - palladium - heterocycles - stereoselectivity - cyclization

    References and Notes

  • 1 Perron F. Albizati KF. Chem. Rev.  1989,  89:  1617 
    CrossrefGoogle Scholar
  • For isolation, see:
  • 2a Traxler P. Gruner J. Auden JA.
    J. Antibiot.  1977,  30:  289 
    Google Scholar
  • 2b For structural characteri-zation, see: Traxler P. Frittz H. Richter WJ. Helv. Chim. Acta  1977,  60:  578 
    Google Scholar
  • 3a Barrett AGM. Pena M. Aillardsen JA. J. Org. Chem.  1996,  61:  1082 
    Google Scholar
  • 3b Denmark SE. Regens CS. Kobayashi T. J. Am. Chem. Soc.  2007,  129:  2774 
    Google Scholar
  • 4a Wu Q. Simons C. Synthesis  2004,  1533 
    Google Scholar
  • 4b Kool ET. Acc. Chem. Res.  2002,  35:  936 
    Google Scholar
  • 5 Yamamoto Y. Hashimoto T. Hattori K. Kikuchi M. Nishiyama H. Org. Lett.  2006,  8:  3565 
    CrossrefGoogle Scholar
  • 6 Mori K. Kiyota H. Liebigs Ann. Chem.  1992,  989 
    CrossrefGoogle Scholar
  • 7 Song ZJ. Zhao M. Desmond R. Devine P. Tschaen DM. Tillyer R. Frey L. Heid R. Xu F. Foster B. Li J. Reamer R. Volante R. Grabowski EJ. Dolling UH. Reider PJ. Okada S. Kato Y. Mano E. J. Org. Chem.  1999,  64:  9658 
    CrossrefGoogle Scholar
  • 8 Miyazawa M. Hirose Y. Narantsetseg M. Yokoyama H. Yamaguchi S. Hirai Y. Tetrahedron Lett.  2004,  45:  2883 
    CrossrefGoogle Scholar
  • 9 Yu W. Mei Y. Hua Z. Jin Z. Org. Lett.  2004,  6:  3217 
    CrossrefPubMedGoogle Scholar
  • 11 Uenishi J. Vikhe YS. Kawai N. Chem. Asian J.  2008,  3:  473 
    CrossrefGoogle Scholar
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The stereochemistry of 10a was confirmed unequivocally by single-crystal X-ray diffraction analysis.