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Applications of Allyl and Alkenyl Zirconocenes and Progress Toward the Total Synthesisof Tuberostemonone

Pierce, Joshua Glenn (2009) Applications of Allyl and Alkenyl Zirconocenes and Progress Toward the Total Synthesisof Tuberostemonone. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

This dissertation describes the development of several novel chemical reactions employing allyl and alkenyl zirconocenes. These diverse nucleophiles were employed in thesynthesis of a variety of biologically and chemically important molecules. Initially, allyl zirconocenes were employed for the addition to imines, thereby providing rapid access tofunctionalized homoallylic amines. We were later able to employ alkenyl zirconocenes in both the construction of C-glycosidic bonds and the addition to chiral imines. The power of thesetransformations was realized by a rapid and stereoselective synthesis of an immunostimulant agent and its analogs. Biological evaluation of these compounds showed encouraging activity against malaria. Small molecule radioprotectant agents have also been developed and show promising potential for therapeutic use. Finally, we were able to install key stereocenters of the Stemona alkaloid tuberostemonone.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Pierce, Joshua Glennjoshuapierce6@me.com
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberDoemling, Alexasd30@pitt.eduASD30
Committee MemberCurran, Denniscurran@pitt.eduCURRAN
Committee MemberGreenberger, Joelgreenbergerjs@upmc.eduJOELG
Committee MemberNelson, Scottsgnelson@pitt.eduSGNELSON
Date: 28 January 2009
Date Type: Completion
Defense Date: 17 November 2008
Approval Date: 28 January 2009
Submission Date: 10 December 2008
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
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: allylic amines; chemistry; immunostimulant; natural products
Other ID: http://etd.library.pitt.edu/ETD/available/etd-12102008-204416/, etd-12102008-204416
Date Deposited: 10 Nov 2011 20:10
Last Modified: 19 Dec 2016 14:38
URI: http://d-scholarship.pitt.edu/id/eprint/10292

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