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Synthetic Studies Toward Complex Polycyclic Natural Products

Cao, Liming (2018) Synthetic Studies Toward Complex Polycyclic Natural Products. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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The first chapter of this dissertation describes the use of an intramolecular Staudinger/aza-Wittig reaction in the synthesis of 1,2,5,6-tetrahydro-1,2,4-triazines, a structural motif of the natural product noelaquinone. The DEF ring system of noelaquinone was prepared in 13 steps and 2% overall yield with key steps featuring a Cu(I)-catalyzed C-arylation and the controlled acidic hydrolysis of the PMB protective group.
The second chapter describes the investigation of reactions between methyl 3-oxo-2-oxabicyclo[2.2.0]hexane-6-carboxylate and an indolo-indoline dimer in the presence of BF3·OEt2. Two tricyclic-fused heterocyclic products and a diene carboxylic acid have been obtained through a ring opening process, a retro-[2+2] cycloaddition, and a conjugate addition from the indole fragment.
The third chapter describes progress toward the total synthesis of haouamine A. Several routes to the marine alkaloid have been attempted. The challenges associated with the late stage lactam reduction, epoxidation, and aromatization strategy to prepare the necessary tetrahydropyridine and aza-cyclophane moieties are discussed.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Cao, Liminglic57@pitt.edulic57
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.edupwipf
Committee MemberKoide, Kazunorikoide@pitt.edukoide
Committee MemberHuryn, Donnahuryn@pitt.eduhuryn
Committee MemberLiu, Xinyuxinyuliu@pitt.eduxinyuliu
Date: 28 June 2018
Date Type: Publication
Defense Date: 27 March 2018
Approval Date: 28 June 2018
Submission Date: 12 April 2018
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 269
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: Natural Product Total Synthesis Noelaquinone Haouamine Heterocycle
Date Deposited: 28 Jun 2018 14:53
Last Modified: 28 Jun 2018 14:53


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