Model Studies towards the Total Synthesis of GKK1032s, Novel Antibiotic Anti-Tumor Agents: Enantioselective Synthesis of the Alkyl Aryl Ether Portion of GKK1032s

An enantioselective synthesis of an alkyl aryl ether portion of GKK1032s, novel antibiotic anti-tumor agents, was achieved via Mitsunobu reaction between a sterically congested indenol derivative and a p-substituted phenol derivative. The indenol derivative, the key substrate for the Mitsunobu reaction, was efficiently synthesized starting from the known indanone derivative through regio- and stereoselective methylation, Saegusa oxidation, and carbonyl transposition as the pivotal steps.