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A stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres

โœ Scribed by Robert V. Hoffman; Junhua Tao

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
242 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A simple, stel'eoc~ntrollod synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. The method is short (6 sleps) and diastereoselective (85-95% de) and enantioselective (>95% ee).

๐Ÿ“œ SIMILAR VOLUMES

A simple, stereoselective synthesis of k
A simple, stereoselective synthesis of ketomethylene dipeptide isosteres
โœ Robert V. Hoffman; Junhua Tao ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 492 KB

An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-~/-ketoesters) from Cbz-protected amino acids and scalemic 2-triflyloxy esters has been developed. The method is short (three steps), efficient, and hi

Synthesis of hydroxyethylene and ketomet
Synthesis of hydroxyethylene and ketomethylene dipeptide isosteres
โœ Mark W. Holladay; Daniel H. Rich ๐Ÿ“‚ Article ๐Ÿ“… 1983 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 210 KB

A general stereo-directed synthesis of "ketomethylene" and "hydroxyethylene" dipeptide isosteres is reported. Peptides containing the amino acids, (2&%)-5-amino-4-oxo-2,8dimethyloctanoic acid (the "ketomethylene" analog of L-Leu-L-Ala), and (2&,5z)-5-amino-4-hydroxy-2,8-dimethyloctanoic acid (the "h

A short, efficient synthesis of monofluo
A short, efficient synthesis of monofluoro ketomethylene peptide isostere core units
โœ Robert V. Hoffman; James E. Saenz ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 194 KB

Monofluoro ketomethylene peptide isosteres can be prepared by a four step sequence from earboxylic acids in satisfactory overall yields (30-60%). Fluorine is introduced by electrophilic fluorination of a ~-ketoester enolate with SelectFluor TM.