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American Chemical Society, Journal of Organic Chemistry, 6(70), p. 2325-2328, 2005

DOI: 10.1021/jo048172s

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General Approach to Glycosidase Inhibitors. Enantioselective Synthesis of Deoxymannojirimycin and Swainsonine

Journal article published in 2005 by Rubén Martín, Caterina Murruzzu, Miquel A. Pericàs ORCID, Antoni Riera ORCID
This paper is available in a repository.
This paper is available in a repository.

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Abstract

[reaction: see text] Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbamate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.