Towards the total synthesis of amphidinol 3

Amphidinols are intriguing amphiphilic architectures exhibiting a variety of biological actions, including antifungal, hemolytic, cytotoxic and ichthyotoxic activities. These properties derive from the disturbance of the arrangement of the lipid bilayer of the targeted cells. The third member of the family, amphidinol 3 was discovered in 1996 and is, to date, the only amphidinol whose stereochemistry is fully established. The synthesis of the C15-C30 polyol domain, as well as the preparation of the C31-C40 trans-configured tetraydropyran will be discussed throughout this work.