Synthesis of Piperovatine

Panjab University, Regional Centre for Post Graduate Studies, Rothak.

Department of Chemistry, Panjab University, Chandigarh-14.

Manuscript received 9 April 1974 ; revised 16 July 1974 ; accepted 18 July 1974

The reaction of phosphonate of ethyl crotonate with p-methoxyphenyl acetaldehyde (V) yields ethyl 6(p-methoxyphenyl)-hexa trans-2, trans-4 dienoate (VI). This unsaturated ester (VI) on hydrolysis and treatment with thionyl chloride followed by the reaction of isobutyl amine gives piperovatine. The aldehyde (V) was obtained from the corresponding acid (II),, through its chloride (III), anilide (IV), followed by LiAlH₄ reduction of the anilide.