The first enantioselective synthesis of imino-deoxydigitoxose and protected imino-digitoxose by using l-threonine aldolase-catalyzed aldol condensation |
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Authors: | Toshihiro Nishiyama Tetsuya Kajimoto Swapnil S Mohile Noboru Hayama Teppei Otsuda Minoru Ozeki Manabu Node |
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Institution: | Kyoto Pharmaceutical University, 21st Century COE Program, 1 Shichono-cho, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan |
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Abstract: | The first enantioselective synthesis of protected imino-digitoxose (?)-16 was attained starting with a synthetic intermediate of polyoxin C prepared by the l-threonine aldolase-catalyzed aldol condensation of (2S,3S)-2,3-O-isopropyriden-4-penten-1-al 8 and glycine. The strategy took advantage of an intramolecular nucleophilic attack by a Cbz-protected amino group on the hemiacetal carbon, a side reaction in the synthesis of natural products, for the formation of the piperidine ring of the imino-sugar. Imino-deoxydigitoxose (+)-18 was also synthesized from (?)-16 by reduction and acid hydrolysis. |
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