Palladium (II)-catalyzed Stereoselective Cyclization to the Ether and its Application to the Synthetic Studies of Yessotoxin

The polycyclic ether marine toxin "yessotoxin" was isolated from the digestive glands of the scallop Patinopecten yessoensis, which shows diarrhetic shellfish poisoning. This toxin is produced by dinoflagellates, and consisted of the unique structures, which involves the ladder-shaped and trans-fused polycyclic ethers. Thus several groups have been reported the synthetic studies of this toxin. In recent years, we have been studying the Pd (II)-catalyzed cyclization and its application to the synthesis of natural products, especially aza sugars and alkaloids. Herein we describe the Pd (II)-catalyzed cyclization to ether and its application to the synthetic studies of yessotoxin. This reviews the activation of the allyl alcohol and the stereoselective construction of cyclic ethers by using Pd (II) catalyst. We attained the AB, CD and JK ring systems of yessotoxin, respectively. And the medium-size ether construction is also involved.