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Paper | Special issue | Vol 59, No. 2, 2003, pp.547-571
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S52
Synthesis of Ketosyl Spiro-isoxazolidine by 1,3-Dipolar Cycloaddition of 1-Methylenesugars with Nitrones —A New Access to C-Glycosyl Amino Acids

Xiaoliu Li, Hideyo Takahashi, Hiro Ohtake, and Shiro Ikegami*

*School of Pharmaceutical Sciences, Teikyo University, 1091-1, Sagamiko, Kanagawa 199-0195, Japan

Abstract

The 1,3-dipolar cycloaddition reactions of 1-methylenesugars (1a~c) with nitrones (2 and 5) were carried out diastereoselectively under the catalysis of BF3·Et2O at low temperature and afforded the α-stereoselective spiro ketosyl isoxazolidines in good to excellent yields. The reductive isoxazolidine ring-opening of the spiro moiety with the treatment of zinc and acetic acid resulted in a new kind of C-glycosyl amino acid possessing a ketose form, providing an access to C-glycosyl amino acids. The structures of the synthesized compounds were confirmed by the spectroscopic analyses.