Chemoenzymatic Formal Total Synthesis of (-)-Bestatin

Brent D. Feske; Jon D. Stewart

doi:10.1016/j.tetasy.2005.08.022

Chemoenzymatic Formal Total Synthesis of (-)-Bestatin

Brent D. Feske, Jon D. Stewart

Biochemistry, Chemistry & Physics

University of Florida

Research output: Contribution to journal › Article › peer-review

22 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 language	American English
Journal	Tetrahedron: Asymmetry
Volume	16
DOIs	https://doi.org/10.1016/j.tetasy.2005.08.022
State	Published - Jan 1 2005

Disciplines

Chemistry

Keywords

(-)-Bestatin
Chemoenzymatic formal
Total synthesis

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https://doi.org/10.1016/j.tetasy.2005.08.022

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title = "Chemoenzymatic Formal Total Synthesis of (-)-Bestatin",

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.",

keywords = "(-)-Bestatin, Chemoenzymatic formal, Total synthesis",

author = "Feske, \{Brent D.\} and Stewart, \{Jon D.\}",

year = "2005",

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doi = "10.1016/j.tetasy.2005.08.022",

language = "American English",

volume = "16",

journal = "Tetrahedron: Asymmetry",

publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Chemoenzymatic Formal Total Synthesis of (-)-Bestatin

AU - Feske, Brent D.

AU - Stewart, Jon D.

PY - 2005/1/1

Y1 - 2005/1/1

N2 - 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.

AB - 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.

KW - (-)-Bestatin

KW - Chemoenzymatic formal

KW - Total synthesis

UR - https://digitalcommons.georgiasouthern.edu/chem-facpubs/136

UR - https://doi.org/10.1016/j.tetasy.2005.08.022

U2 - 10.1016/j.tetasy.2005.08.022

DO - 10.1016/j.tetasy.2005.08.022

M3 - Article

VL - 16

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

ER -

Chemoenzymatic Formal Total Synthesis of (-)-Bestatin

Abstract

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Keywords

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