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Paper | Regular issue | Vol 34, No. 10, 1992, pp.1935-1947
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6112
Synthesis of 1,6:3,4-Dianhydro-β-D-talopyranose from Levoglucosenone: Epoxidation of Olefin via trans-Iodoacetoxylation

Katsuya Matsumoto,* Takashi Ebata,* Koshi Koseki, Koji Okano, Hiroshi Kawakami, and Hajime Matsushita

*Life Science Research Laboratory, Japan Tobacco Inc., 6-2, Umegaoka, Midori-ku, Yokohama, Kanagawa 227, Japan

Abstract

Levoglucosenone (1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose, 1) was converted to give 1,6:3,4-dianhydro-β-D-talopyranose (8) in good yield through stereoselective trans-iodoacetoxylation followed by basic hydrolysis.