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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
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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

10

The stereochemistry of 10a was confirmed unequivocally by single-crystal X-ray diffraction analysis.