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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
- Authors
- Choi, Hwan Geun; Park, Dong-Sik; Lee, Won Koo; Sim, Taebo
- Issue Date
- 23-10월-2013
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- D-AB1/L-AB1; D-DIX/L-DIX; Natural product; Efficient synthesis; Chiral aziridines
- Citation
- TETRAHEDRON LETTERS, v.54, no.43, pp.5775 - 5777
- Indexed
- SCIE
SCOPUS
- Journal Title
- TETRAHEDRON LETTERS
- Volume
- 54
- Number
- 43
- Start Page
- 5775
- End Page
- 5777
- ISSN
- 0040-4039
- 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. (c) 2013 Elsevier Ltd. All rights reserved.
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