Chemistry: Faculty Publications (1990-2023)
Chemoenzymatic Formal Total Synthesis of (-)-Bestatin
Document Type
Article
Publication Date
1-1-2005
Publication Title
Tetrahedron: Asymmetry
DOI
10.1016/j.tetasy.2005.08.022
ISSN
0957-4166
Abstract
A highly stereoselective, enzymatic reduction of an α-chloro-β-keto ester provided the key intermediate for a total synthesis of the α-hydroxy-β-amino acid moiety of (−)-bestatin. The reduction product was cyclized to a glycidic ester that was opened in a Ritter reaction with benzonitrile, affording a trans-oxazoline, which was hydrolyzed under acidic conditions to the target molecule.
Recommended Citation
Feske, Brent D., Jon D. Stewart.
2005.
"Chemoenzymatic Formal Total Synthesis of (-)-Bestatin."
Tetrahedron: Asymmetry, 16 (18): 3124-3127: Elsevier.
doi: 10.1016/j.tetasy.2005.08.022 source: https://www.sciencedirect.com/science/article/pii/S0957416605006348?via%3Dihub
https://digitalcommons.georgiasouthern.edu/chem-facpubs/136
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