Chemoenzymatic Formal Total Synthesis of (-)-Bestatin

Brent D. Feske, Jon D. Stewart

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

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.

Original languageAmerican English
JournalTetrahedron: Asymmetry
Volume16
DOIs
StatePublished - Jan 1 2005

Keywords

  • (-)-Bestatin
  • Chemoenzymatic formal
  • Total synthesis

DC Disciplines

  • Chemistry

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