Two bis-THF Annonaceous Acetogenin structures were synthesised, one of which corresponded to the cytotoxic antitumour compound membranacin. Both derived from key epoxide intermediate, which was synthesized via the chiral auxiliary directed oxidative cyclisation of 1,5,9-trienedioate by potassium permanganate. The second THF ring was installed using a Sharpless asymmetric epoxidation and epoxide opening strategy. A number of intermediates were designed with the potential for future library synthesis of natural product analogues. The combination of the permanganate oxidation and Kennedy's perrhenate cyclisation of bis-homoallylic alcohols was used to synthesise simple bis-THF model. This combined strategy allows access to the acetogenin bis-THF core.