Synthesis of ω-Acetyl-α-methylenpolyene Carboxylic Esters

Article abstract of DOI:10.1002/prac.19943360806

The α-methylenpolyene carboxylic acids 1 and 2 are highly active against Gram-positive bacteria.If this activity arises from an interference with the cell membranes, then an abrupt change in biological properties is to be expected with growing chain length of simple model compounds.To make these tests possible, we describe here the synthesis of a series of homologue esters of type 40.Their synthesis was achieved by Wittig reactions of polyene α,ω-dialdehydes 6 with acetylmethylentriphenylphosphoran 5a and the protected carboxymethylmethylen triphenylphosphonium salt 8.