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Stereoselective synthesis of conformationally constrained (2S,3S)-3-hydroxyornithine
Affiliation:1. Ufa Institute of Chemistry of the Russian Academy of Sciences, Prospect Oktyabrya 71, 450054 Ufa, Russian Federation;2. Bashkir State University, Zyaki Validi 32, 450074 Ufa, Russian Federation;1. University of Pardubice, Faculty of Chemical Technology, Doubravice 41, 53210 Pardubice, Czech Republic;2. University of Rostock, Institute of Physics, Wismarsche Str. 43–45, 18051 Rostock, Germany;1. Department of Chemistry, Sir Parashurambhau College, Sadashiv Peth, Pune 411030, India;2. Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India;3. Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
Abstract:A convenient and efficient route is described for the highly stereoselective synthesis of δ-amino protected and conformationally restricted (2S,3S)-3-hydroxyornithine through the N-benzylnitrone adduct to the α,β-unsaturated bicyclic lactam 2 derived from (S)-pyroglutaminol.
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