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Synthesis of the monofluoro ketone peptide isostere

โœ Scribed by Garrett, Garry S.; Emge, Thomas J.; Lee, Susannie C.; Fischer, Elaine M.; Dyehouse, Karyn; McIver, John M.

Book ID
127142237
Publisher
American Chemical Society
Year
1991
Tongue
English
Weight
471 KB
Volume
56
Category
Article
ISSN
0022-3263

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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.

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Title compounds of type (VII) (6 examples) are readily prepared following the 4-step sequence presented. The introduction of the fluorine substituent is best achieved using selectfluor under the optimized conditions shown.

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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).