Abstract
Maitotoxin, a marine polycyclic ether isolated from the dinoflagellate Gambierdiscus toxicus, is the most toxic and largest natural product known to date except for biopolymers such as protein or polysaccharides. The skeletal novelty, complexity, and biological activity of maitotoxin have attracted the attention of chemists and biologists.We have already developed the SmI2-induced reductive cyclization to synthesize the trans-fused ether ring system stereoselectively. We now report the stereoselective syntheses of the BCDE-ring system of maitotoxin. The key steps involve 6-endo-cyclization of methylepoxide, SmI2-induced cyclization, SmI2-induced double cyclization, and double hydroxylation of TMS enol ether.
