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- Title
Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid.
- Authors
Simirgiotis, Mario J.; Vallejos, Javier; Areche, Carlos; Sepúlveda, Beatriz
- Abstract
An enantioselective total synthesis of the natural amino acid (2S,4R,5R)-4,5-dihydroxy- pipecolic acid starting from D-glucoheptono-1, 4-lactone is presented. The best sequence employed as a key step the intramolecular nucleophilic displacement by an amino function of a 6-O-p-toluene-sulphonyl derivative of a methyl D-arabino-hexonate and involved only 12 steps with an overall yield of 19%. The structures of the compounds synthesized were elucidated on the basis of comprehensive spectroscopic (NMR and MS) and computational analysis.
- Subjects
ASYMMETRIC synthesis; AMINO acid biotechnology; PEPTIDES; CHEMICAL reactions; CHEMICAL processes; CHEMICAL energy; CATALYSTS
- Publication
Molecules, 2014, Vol 19, Issue 12, p19516
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules191219516