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 (Unpublished)

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Abstract

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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Details

Item Type:	University of Pittsburgh ETD
Status:	Unpublished
Creators/Authors:	Creators Email Pitt Username ORCID Cao, Liming lic57@pitt.edu lic57
ETD Committee:	Title Member Email Address Pitt Username ORCID Committee Chair Wipf, Peter pwipf@pitt.edu pwipf Committee Member Koide, Kazunori koide@pitt.edu koide Committee Member Huryn, Donna huryn@pitt.edu huryn Committee Member Liu, Xinyu xinyuliu@pitt.edu xinyuliu
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
URI:	http://d-scholarship.pitt.edu/id/eprint/34268

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