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

Ken-ichiro Awasaguchi; Masahiro Miyazawa; Ikuyo Uoya; Koichi Inoue; Koji Nakamura; Hajime Yokoyama; Hiroko Kakuda; Yoshiro Hirai

doi:10.1055/s-0030-1258560

LETTER

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

Ken-ichiro Awasaguchi^a, Masahiro Miyazawa*^b, Ikuyo Uoya^b, Koichi Inoue^b, Koji Nakamura^b, Hajime Yokoyama^b, Hiroko Kakuda^c, 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

Abstract

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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

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Referenzen

References and Notes

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