First efficient synthesis of (±)-erythro-roccellic acid

Abstract

An easy, four-step route to (±)-erythro-2-dodecyl-3-methylbutanedioic acid (roccellic acid, 9) with 60% overall yield has been described. Wittig reaction of the citraconimide–TPP adduct with dodecanal furnished the mixture of (E)- and (Z)-isomers 3 and 4, which, on base-catalysed exocyclic to endocyclic double bond isomerisation, yielded maleimide 5. Catalytic cis-hydrogenation of 5 using Adam's platinum dioxide catalyst followed by acid-catalysed hydrolysis of formed succinimide 8 gave desired (±)-erythro-roccellic acid 9.