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Design and Synthesis of Organic Molecules with New Physical and Biological Properties

Ma, Gil (2005) Design and Synthesis of Organic Molecules with New Physical and Biological Properties. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Poly(cyclic urea) compounds were synthesized and tested as substitutes of hexamethylphosphoramide (HMPA). HMPA is a potent carcinogen but demonstrates excellent properties as an additive in organometal chemistry. The poly(cyclic urea), which showed similar properties to HMPA in solution, was attached to a variety of resins in an effort to create a new polymer-supported reagent. Polymer-supported HMPA was also prepared by suspension polymerization. In diverse reactions, these reagents showed very similar properties to HMPA, were easily removed by filtration and could be recycled without loss of chemical activity.Highly functionalized spiroketals were designed and synthesized as mimics of calyculin A, a known protein phosphatase inhibitor. Regio- and stereoselective reductions, hetero-Diels-Alder reactions and spiroketalizations gave eight diastereomeric spiroketal compounds. Additionally, through asymmetric crotylations, phosphorylations and cross-metathesis, a series of new phosphoric acid compounds were also synthesized.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberLazo, John S.lazo@pitt.eduLAZO
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Committee MemberNelson, Scottsgnelson@pitt.eduSGNELSON
Date: 5 October 2005
Date Type: Completion
Defense Date: 3 June 2005
Approval Date: 5 October 2005
Submission Date: 13 June 2005
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: HMPA; polymer-supported reagent; protein phosphatase inhibitor; sprioketal
Other ID:, etd-06132005-094748
Date Deposited: 10 Nov 2011 19:47
Last Modified: 15 Nov 2016 13:44


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