An efficient synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol and 1,4-dideoxy-1,4-imino-d- and l-xylitol from chiral aziridines |
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| Authors: | Hwan Geun Choi Dong-Sik Park Won Koo Lee Taebo Sim |
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| Institution: | 1. Future Convergence Research Division, Korea Institute of Science and Technology, PO Box 131,Cheongryang, Seoul 130-650, Republic of Korea;2. Department of Chemistry, Sogang University, Seoul 121-742, Republic of Korea;3. KU-KIST Graduate School of Converging Science and Technology, 145, Anam-ro, Seongbuk-gu, Seoul 136-713, Republic of Korea |
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| Abstract: | A highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol (d-AB1, 1 and l-AB1, 3) and 1,4-dideoxy-1,4-imino-d- and l-xylitol (d-DIX, 2 and l-DIX, 4) starting from commercially available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered iminosugar ring formation. The facile use of recrystallization to generate pure diastereomers makes the routes more amenable to large-scale synthesis. |
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| Keywords: | d-AB1/l-AB1 d-DIX/l-DIX Natural product Efficient synthesis Chiral aziridines |
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