Asymmetric conjugate addition reactions for small natural product synthesis

ORGN 564

Richard J. Mullins, mullinsr@xavier.edu, Department of Chemistry, Xavier University, 3800 Victory Parkway, Cincinnati, OH 45207-4221
The well-studied use of chiral, non-racemic oxazolidinone auxiliaries for asymmetric conjugate addition reactions in small molecule synthesis has emerged as a theme in our research group. Specifically, the Lewis acid promoted conjugate addition of allylic stannanes is being applied to the synthesis of the insect trail pheromone lasiol and the potent antitumor agent kalkitoxin. Additionally, the conjugate addition of organocopper reagents for installation of a hydroxymethyl equivalent is being applied toward the synthesis of the small molecules pilosine, pilocarpine and lavandulol. Our progress toward the syntheses of these biologically important molecules will be presented.