Studies Toward the Total Synthesis of Saudine : Simple and Stereoselective Synthesis of a Model Caged Ketal Backbone

The synthesis of the tetracyclic mainframe containing the caged ketalic backbone of saudin was accomplished through a straight forward sequence starting from α-tetralone. The sequence included the stereoselective preparation of a key epoxy alcohol that allowed, by means of an intramolecular radical cyclisation, the total control of the relative stereochemistry of four consecutive chiral centers.