Abstract:

Dinoflagellates of the genus Amphidinium posses a particularly prolific biosynthetic machinery. For instance, over thirty macrolides have been isolated from Amphidinium strains, displaying extremely potent cytotoxicity against tumor cell lines. Among them, the Amphidinolide T family comprises 19-membered macrolactones possessing seven or eight stereogenic centers, a highly substituted tetrahydrofuran ring, an a−hydroxy ketone, an exocyclic methylene group and a homoallylic ester linkage. Due to their high biological activity and intriguing polyoxygenated structure, we became interested in their preparation and designed a chemoenzymatic approach to the C14-C21 fragment, using as starting material cyclohexadienediol 1 produced by biotransformation of bromobenzene, as shown in Fig.1.