Synthesis of new optically active propargylic fluorides and application to the enantioselective synthesis of monofluorinated analogues of fatty acid metabolites.
A new approach to obtain optically active unsaturated or polyunsaturated systems with a single fluorine atom in an allylic or propargylic position is reported. Central to this strategy is the high regio- and stereocontrol observed during the fluorination of propargylic alcohols allowing a short and efficient synthesis of 1. Further, simple functional group transformations gave the enals 2 and 3. These three key intermediates were used for the preparation of optically active monofluorinated analogues of fatty acid metabolites.
Prakesch
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ENSCR, Laboratoire de Synthèses et Activations de Biomolécules, CNRS UMR 6052, Avenue du Général Leclerc, 35700 Rennes, France.
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D000473:Alkanes / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D005227:Fatty Acids / Q000737:chemistry* / Q000378:metabolism; D005231:Fatty Acids, Unsaturated / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000473:Alkanes; D005227:Fatty Acids; D005231:Fatty Acids, Unsaturated; D007202:Indicators and Reagents; D005459:Fluorides