Synthesis of d- and l-Deoxymannojirimycin via an Asymmetric Aminohydroxylation of Vinylfuran
- 16 January 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (3) , 401-404
- https://doi.org/10.1021/ol006907j
Abstract
[figure: see text] The Sharpless catalytic asymmetric aminohydroxylation has been applied to 2-vinylfuran, producing beta-hydroxyfurfurylamine 5a with enantioexcess of > 86% and 21% yield from furfural. The Cbz and TBS protected amino alcohol 5a was converted into both the D- and L-isomers of deoxymannojirimycin (DMJ) and deoxygulonojirimycin in five to seven steps and 48% and 66% overall yields. The key steps include the use of an aza-Achmatowicz reaction, a diastereoselective Luche reduction, diastereoselective dihydroxylation, and a tandem Cbz deprotection/reductive amination.Keywords
This publication has 19 references indexed in Scilit:
- Carbohydrate Mimetics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological RecognitionAngewandte Chemie International Edition in English, 1999
- Theory Rules Out a [2 + 2] Addition of Osmium Tetroxide to Olefins as Initial Step of the Dihydroxylation ReactionAngewandte Chemie International Edition in English, 1996
- Synthesis of a 2-Hydroxymethyl-dihydropyridone-System as a Flexible Building Block for the Preparation of AzasugarsTetrahedron Letters, 1995
- Expeditious Synthesis of Aza sugars by the Double Reductive Amination of Dicarbonyl SugarsThe Journal of Organic Chemistry, 1994
- The Synthesis of (2S,3R)-2-Hydroxymethylpiperidin-3-ol, a Fragment of the Alkaloid SwainsonineAustralian Journal of Chemistry, 1990
- Inhibition of Human HT29 Colon Carcinoma Growth In Vitro and In Vivo by Swainsonine and Human Interferon-α2JNCI Journal of the National Cancer Institute, 1989
- Chemoenzymic synthesis of chiral furan derivatives: useful building blocks for optically active structuresThe Journal of Organic Chemistry, 1988
- CASTANOSPERMINE AND OTHER PLANT ALKALOID INHIBITORS OF GLUCOSIDASE ACTIVITY BLOCK THE GROWTH OF HIVThe Lancet, 1987
- A Four-Step Synthesis of 1-Deoxynojirimycin with a Biotransformation as Cardinal Reaction StepAngewandte Chemie International Edition in English, 1981
- Monosaccharide mit stickstoffhaltigem Ring, XIII. Synthese und Reaktionen von Keto‐piperidinosenEuropean Journal of Inorganic Chemistry, 1967