(+)-desoxoprosopinine a model for the total asymmetric synthesis of prosopis alkaloids /

by 1971- Sandelier, Matthew J.

SANDELIER, MATTHEW J.: (+)-Desoxoprosopinine: A Model for the Total Asymmetric Synthesis of Prosopis Alkaloids. (Under the direction of Dr. Daniel L. Comins.) This work develops a general synthesis of the Prosopis africana alkaloids, using a chiral auxiliary-mediated process. Enantiopure N-acyldihydropyridones were produced and used as intermediates, targeting (+)-desoxoprosopinine as a synthetic model for those alkaloids. The orientation of all three stereocenters was highly controlled, with the synthesis of intermediate 75, just short of the target, in 7 steps with a 13.8% overall yield. (+)-DESOXOPROSOPININE: A MODEL FOR