抄録
Gambierol is a marine polycyclic ether isolated as a neurotoxin from the cultured cells of the ciguatera causative dinoflagellate Gambierdiscus toxicus. The structure consists of a trans-fused octacyclic polyether containing three hydroxy groups and a partially skipped triene side chain. The characteristic structure and potent biological activity make gambierol a challenging synthetic target. The synthesis of the ABCDEF ring system of gambierol is presented.
The synthesis started from the preparation of the D ring using an oxiranyl anion strategy and the following construction of the C and B rings by radical cyclization and hydroxy-epoxide cyclization, respectively. The A ring was constructed by reductive etherification to give the ABCD ring fragment. Further application of the oxiranyl anion strategy followed by ring expansion reaction and vinyl radical cyclization provided the ABCDEF ring system of gambierol.
