Synthesis of molecules of biological interest. Contribution to the synthesis of bastadin.

SYNTHESIS OF MOLECULES OF BIOLOGICAL INTEREST. CONTRIBUTION TO THE SYNTHESIS OF BASTADIN.C.Decamps1, L. Niemiroski, A-L. Hantson, M. De MeyerThe metabolites are a biochemical area whose interest is in constant progression. Indeed, these molecules are biologically active and are used in therapeutic treatments. The bastadin are an ever-growing family of marine natural products isolatd from sponges of the order Verongida. This kind of molecule, are macromolecules with two amides bonds and two diphenyl ethers linkage and represent an important class of compounds recongized as potential anticancer drugs. Those compounds exhibit antifouling, antiviral, cytotoxicity, antifungal and antibacterial activities (1,2,3). It's involved in the mechanism governing the release of calcium in the cell. The latter property is very interesting and requires the industrial production of bastadin.
A complete synthesis scheme of bastadin was developed by C. Couladouros (4) in homogeneous phase, but il requires a lot of steps (20-30) with an overall yield of synthesis extremely low (3.5 %).
This work focused on the development and implementation of an original synthesis scheme of bastadin. This synthesis is made in heterogeneous phase from dopamine. Indeed, the left fragment of the bastadin can be achivied via a coupling reaction in basic medium between modified dopamine on solid support ans a diaryliodonium salt. Then, the macro cyclization of the molecule is obtained by condensation reaction of amines on the left side with acids from the right side.