An enantioselective route for the synthesis of the α-glucosidase inhibitor DAB-1 is presented. Because DAB-1, and its derivatives, is known to interfere with the activity of α-glucosidase, this natural product has potential applications in medicine for the treatment of diabetes, cancer, and genetic disorders. Our novel approach to the total synthesis of DAB-1 utilizes the almond enzyme, oxynitrilase, to reliably induce asymmetry in our achiral starting material, crotonaldehyde. The key step in our strategy is a substitutive transposition via a palladium-catalyzed 1, 3-chiral shift. This reaction allows for the introduction of the nitrogen functionality with complete stereochemical fidelity. Further manipulation of the enantiomerically pure backbone should ultimately afford the title compound, DAB-1.
Whalen, Meghan, "AnEnantioselectiveSynthesisofDAB-1" (2011). URC Student Scholarship.
Kenneth T. and Eileen L. Norris Foundation Science Scholars Program