A synthesis of freelingyne

Abstract

Acetylation of the tertiary alcohol prepared from the Reformatsky reaction of 1-bromo-3-(3'-furyl)prop-2-yne with (2Z,4E)-2-methyl-6-oxohepta-2,4-dien-4-olide gave the acetate. Flash vacuum pyrolysis of the tertiary acetate gave a mixture of predominantly two isomers, one of which was freelingyne, (2Z,4Z,6E)-9-(3'-furyl)-2,6-dimethylnona-2,4,6-trien-8-yn-4-oide (1). The synthesis of the phenyl analogues is also described.