%0 Generic
%9 Doctoral Dissertation
%A George Rosenker, Kara M.
%D 2014
%F pittir:19989
%K palladium catalysis, palladium cross-coupling, heterocycles, regioselectivity, quinazoline, Cdc25B inhibitor, isoquinoline, protein kinase D, small molecule inhibitor, pyrimidine, pyridine, CID755673, thiazepinothiophenopyrimidinone, chemical diversity, hydrozirconation, isoindolinones, metathesis, N-acyliminium ion, stemona alkaloid, sessilifoliamide C, lactam
%T Regioselective Functionalizations of Heterocycles and Applications in Methodology, Medicinal Chemistry, and Natural Product Synthesis
%U http://d-scholarship-dev.library.pitt.edu/19989/
%X 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.