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Paper | Special issue | Vol 74, No. 1, 2007, pp.283-292
Published online, 3rd July, 2007
DOI: 10.3987/COM-07-S(W)5
Palladium(II)-Catalyzed Cyclization of Urethanes and Its Application to a Total Synthesis of 1-Deoxynojirimycin

Hajime Yokoyama, Hisatake Kobayashi, Masahiro Miyazawa, Seiji Yamaguchi, and Yoshiro Hirai*

*Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama, 930-0887, Japan


We have employed a palladium(II)-catalyzed cyclization of allylic alcohol as a key reaction to achieve a total synthesis of the azasugar 1-deoxynojirimycin from D-mannitol. This reaction should be useful for the stereoselective construction of natural poly-substituted piperidine derivatives.