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Paper | Special issue | Vol 82, No. 1, 2010, pp.531-542
Published online, 8th June, 2010
DOI: 10.3987/COM-10-S(E)24
A Synthetic Approach to Anhydroketopyranoses Having a 6,8-Dioxabicyclo[3.2.1]octane Structure from Ketopyranoses

Takashi Yamanoi,* Kazuhide Matsumura, Sho Matsuda, and Yoshiki Oda

*The Noguchi Institute, 1-8-1, Kaga, Itabashi-ku, Tokyo 173-0003, Japan


We investigated a synthetic approach to the anhydroketopyranoses having a 6,8-dioxabicyclo[3.2.1]octane structure from D-glucopyranose derivatives. The paper describes the nucleophilic addition of the organometallic reagents RLi or RMgX to the glucono-1,5-lactone derivatives to produce the ketopyranose derivatives having a glucose backbone and their intramolecular cyclization into the desired structural anhydroketopyranoses.