A Facile Synthesis of 3,4-Dienamides by the Reaction of Propargyl Alcohols with Cyclic Amide Acetals and Their Stereoselective Rearrangement to 2(E),4(Z)-Dienamides Promoted with Alumina. Total Synthesis of Isochavicine

Article abstract of DOI:10.1021/jo00181a012

Thermal condensation of propargyl alcohols with acetals of 1-acetylpyrrolidine and 1-acetylpiperidine gave 3,4-dienamides in good yields.Alumina promoted the rearrangement of β-allenic amides to 2(E),4(Z)-dienamides stereoselectively.Its application to the synthesis of isochavicine of pepper components is described.Carbon-13 NMR data of these dienamides were obtained.