Abstract by Nathan Steele
Chemistry and Biochemistry
Synthetic Utility of a Chiral Acetamide
Our lab recently developed a novel acetamide with a chiral auxiliary group that has been proven to improve yields and stereoselectivity of several reactions, as well as unlock new synthetic pathways of biologically active molecules, such as Nocardioazine A, a potent anti-cancer drug which treats multi-drug resistence in cancer cells. We are now exploring this novel acetamide's synthetic utility in several reactions, including a Diels-Alder reaction with cyclopentadiene, which yields a stereospecific product. While similar acetamides have been previously used in a Diels-Alder reaction, it has never been done in a stereoselective fashion. Based on our initial tests, the acetamide has effectively worked in this reaction, giving yields near 90%. We believe that our novel acetamide can also be useful in other Diels-Alder reactions with different dienes as well, whose products can lead to the synthesis of other biologically active molecules.