TY - UNPB ID - pittir19989 UR - http://d-scholarship-dev.library.pitt.edu/19989/ A1 - George Rosenker, Kara M. Y1 - 2014/01/30/ N2 - The first two sections of this dissertation describe the development of a regioselective palladium-catalyzed cross-coupling strategy to access highly functionalized heterocycles. This method was successfully applied to 2,4,7-trichloroquinazoline, allowing for the efficient synthesis of quinazolines bearing functionality in specific positions of the heterocyclic ring. The strategy was also extended to 1,3,6-trichloroquinoline for the synthesis and scale-up of a promising 3-aminoisoquinolin-1(2H)-one inhibitor of the dual-specificity phosphatase Cdc25B. The third section of this dissertation describes the design and synthesis of novel thieno[3,2-d]pyrimidine- and thieno[3,2-c]pyridine-based analogs for the inhibition of protein kinase D. A small library of analogs was prepared to assess the structure-activity relationship, and one analog was tested in vivo. The fourth section of this dissertation discusses the investigation of an unusual alkene isomerization process, which occurred during the ring-closing metathesis for the preparation of a tricylic isoindolinone scaffold. The final section of this thesis details our work towards the synthesis of Stemona alkaloids. In particular, a second-generation approach to sessilifoliamide was achieved. KW - palladium catalysis KW - palladium cross-coupling KW - heterocycles KW - regioselectivity KW - quinazoline KW - Cdc25B inhibitor KW - isoquinoline KW - protein kinase D KW - small molecule inhibitor KW - pyrimidine KW - pyridine KW - CID755673 KW - thiazepinothiophenopyrimidinone KW - chemical diversity KW - hydrozirconation KW - isoindolinones KW - metathesis KW - N-acyliminium ion KW - stemona alkaloid KW - sessilifoliamide C KW - lactam TI - Regioselective Functionalizations of Heterocycles and Applications in Methodology, Medicinal Chemistry, and Natural Product Synthesis EP - 237 AV - public ER -