Synthesis of a pyrenophorin precursor, 7-hydroxy-4-oxo-2-octenoic acid by the direct palladium catalyzed coupling of an acrylic tin reagent with an acid chloride

Add time:08/13/2019    Source:sciencedirect.com

A palladium catalyzed coupling reaction of an organotin reagent bearing acrylate functionality with an acid chloride serves as a method to introduce both a ketone and an acrylate functionality into a carbon framework; thus the coupling reaction of 4-t-butyldiphenylsiloxypentanoyl chloride with benzyl 3-tributylstannylacrylate gave a 71% yield of benzyl 7-t-butyldiphenylsiloxy-4-oxo-2-octenoate, which was converted to the ketal of 7-hydroxy-4-oxo-2-octenoic acid, a precursor to the macrolide antibiotic, pyrenophorin.

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