On the synthesis of a fimbrolide

Abstract

The present work is on the total synthesis of a natural compound found in a mixture of secondary metabolite produced by an alga nearby the cost of Australia. The target molecule, the 4-bromo-3-butyl-5-(dibromomethylene)furan-2(5H)-one, has not previously been proposed. The synthetic route described in this thesis uses cheap and readily available starting materials and the target is reached after six synthetic steps. Several new results have been obtained: selective monolithiation of a dibromofuran; Suzuki coupling with butyl boronic acid; a regioselective photo-oxidation of furan. The final step of the synthesis, a dibromoolefination, has not yet been accomplished.