1,4-Induction in aldol reactions of (tertiary α′-alkoxy)methyl ketones: synthesis of the C8–C11 stereotriad of ent-fostriecin

A diastereoselective, boron-mediated aldol process inspired by the natural product fostriecin is described. Using a tertiary α′-stereocenter as the induction element, aldol adducts are provided with high yields, good to excellent levels of diastereoselection, and broad substrate scope. An Evans–Tischencko reduction of the aldol adduct from cinnamaldehyde resulted in the C8–C11 stereotriad of ent-fostriecin.