Stereoselective synthesis of the northern hemisphere of the proposed structure of neaumycin B.

The stereoselective synthesis of the northern hemisphere (C-C) of the purported structure of the extremely potent anticancer natural product neaumycin B has been accomplished. Twelve out of nineteen asymmetry centers have been installed chemically. The key highlights of this synthesis include the Krische iridium catalyzed -diastereoselective carbonyl crotylation, the Crimmins aldol reaction, HWE olefination, CBS reduction, vanadium promoted stereoselective epoxidation, Evans methylation and spiroketalization.