Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form

Synthetic Studies on Haouamine A and Other Biologically Active Heterocycles

Wang, Chenbo (2010) Synthetic Studies on Haouamine A and Other Biologically Active Heterocycles. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

Primary Text

Download (7MB) | Preview


The first section of this dissertation describes the synthesis of a tethered macrocyclic ring system based on the natural product westiellamide. As expected, this system was shown to increase the affinity and ease of complexation to Ag(I) ions as confirmed by NMR and fluorescence Ag(I) titration studies.The second section describes the synthesis of a new series of heterocyclic inhibitors of the BoNT serotype A metalloprotease based on the therapeutic lead NSC 240898. Preliminary structure-activity relationship studies afford detailed insights into the steric and lectrostaticproperties of the pharmacophore of this molecular scaffold. Four of the newly synthesized inhibitors exhibited elevated inhibition against BoNT/A LC when compared to the lead agent.The third section describes an approach towards the total synthesis of haouamine A. A promising route to the marine alkaloid was established, including a highly efficient Suzuki crosscouplingreaction, aldol condensation and aromatization reaction. Several late-stage intermediates were analyzed by X-ray diffraction to provide valuable information about the relationships between conformation and reactivity.


Social Networking:
Share |


Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Wang, Chenbochw17@pitt.eduCHW17
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberGold, Barrygoldbi@pitt.eduGOLDBI
Committee MemberWilcox, Craigdaylite@pitt.eduDAYLITE
Committee MemberKoide, Kazunorikoide@pitt.eduKOIDE
Date: 28 June 2010
Date Type: Completion
Defense Date: 16 December 2009
Approval Date: 28 June 2010
Submission Date: 4 January 2010
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: medicinal chemistry; natural products; total synthesis
Other ID:, etd-01042010-113545
Date Deposited: 10 Nov 2011 19:30
Last Modified: 15 Nov 2016 13:35


Monthly Views for the past 3 years

Plum Analytics

Actions (login required)

View Item View Item