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Regioselective Functionalizations of Heterocycles and Applications in Methodology, Medicinal Chemistry, and Natural Product Synthesis

George Rosenker, Kara M. (2014) Regioselective Functionalizations of Heterocycles and Applications in Methodology, Medicinal Chemistry, and Natural Product Synthesis. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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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.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
George Rosenker, Kara
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberCurran, Dennis P.curran@pitt.eduCURRAN
Committee MemberFloreancig, Paul E.florean@pitt.eduFLOREAN
Committee MemberWang, Q. Janeqjw1@pitt.eduQJW1
Date: 30 January 2014
Date Type: Publication
Defense Date: 7 November 2013
Approval Date: 30 January 2014
Submission Date: 11 November 2013
Access Restriction: 5 year -- Restrict access to University of Pittsburgh for a period of 5 years.
Number of Pages: 237
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: 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
Date Deposited: 30 Jan 2014 21:45
Last Modified: 30 Jan 2019 06:15


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