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Stereocontrolled spirocyclization of exo-glucal derivatives for stereodivergent synthesis of spiro[5.5]ketals |
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| Authors: | Sho Matsuda Akihiro Yoshida Junki Nakagawa Mikio Watanabe Yoshiki Oda Takashi Yamanoi |
| Institution: | 1. The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan;2. Department of Chemistry, School of Science, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa 259-1292, Japan;3. Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan |
| Abstract: | This Letter describes a stereoselective synthetic approach to spiro5.5]ketals from the exo-glucals, constructed from 1-(4-hydroxyalkylidene)-1,5-anhydro-d-glucitol, by spirocyclization based on intramolecular α- and β-selective glycosylation. Stereodivergent synthesis of both α- and β-glucoside of spiro5.5]ketals was attained by combination of chiral d-glucopyranose environment and C-4′ chiral center on the side chain. |
| Keywords: | Glycosylation Cyclization Spiro compound Stereoselective synthesis Lewis acid |
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