Tetrahedron Letters

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

JW Labadie, JK Stille

Index: Labadie, Jeff W.; Stille, J. K. Tetrahedron Letters, 1983 , vol. 24, # 40 p. 4283 - 4286

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Citation Number: 36

Abstract

Abstract 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- ...