Efforts toward the First Enantioselective Total Synthesis of Praziquantel and Synthetic Model Studies on Ecteinascidin 743 by Novel Aromatic C-H Insertion Methodology

The thesis is composed of three chapters. The aim of this thesis is to apply the novel dirhodium perfluorobutyrate-catalyzed intramolecular aromatic C-H insertion methodology to the enantioselective total synthesis of praziquantel and synthetic model studies on ecteinascidin 743, which belongs to th...

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Main Author:	Chen, Chiliu
Format:	Others
Published:	Scholar Commons 2004
Subjects:	Praziquantel Ecteinascidin Isoquinolone Heterocycle Tetrahydroisoquinoline American Studies Arts and Humanities
Online Access:	https://scholarcommons.usf.edu/etd/991 https://scholarcommons.usf.edu/cgi/viewcontent.cgi?article=1990&context=etd

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record_format	oai_dc
spelling	ndltd-USF-oai-scholarcommons.usf.edu-etd-19902019-10-04T05:23:09Z Efforts toward the First Enantioselective Total Synthesis of Praziquantel and Synthetic Model Studies on Ecteinascidin 743 by Novel Aromatic C-H Insertion Methodology Chen, Chiliu The thesis is composed of three chapters. The aim of this thesis is to apply the novel dirhodium perfluorobutyrate-catalyzed intramolecular aromatic C-H insertion methodology to the enantioselective total synthesis of praziquantel and synthetic model studies on ecteinascidin 743, which belongs to the important tetrahydroisoquinoline family. The first introductory chapter deals with the biological significance and previous synthetic methodologies. Our novel methodology is based on dirhodium perfluorobutyrate-catalyzed intromolecular aromatic C-H insertion reaction, which is crucial in the pivotal carbon-carbon bond formation when constructing isoquinolone moiety, which is ubiquitous in numerous natural products of significant biological and pharmacological activities. The second chapter takes on the first enantioselective total synthesis of praziquantel, an antihelmintic drug. Praziquantel is used worldwide to treat schistosomiasis, which has tremendous impact on the global fight on this disease affecting 150 million people. We believe this is the first asymmetric total synthesis to date, which is distinct from previous racemic syntheses reported. We also shed light on the mechanistic aspect of this key reaction to rationalize the superb regioselectivity and stereoselectivity achieved. The third chapter explores the synthetic model studies on ecteinascidin 743, a tetrahydroisoquinolone family natural product with significant antitumor and antimicrobial activities. Several different synthetic routes were attempted, including the N-Methyl and the N-Boc routes, and the results achieved contributed significantly to our final synthetic plan of the target molecule. 2004-03-18T08:00:00Z text application/pdf https://scholarcommons.usf.edu/etd/991 https://scholarcommons.usf.edu/cgi/viewcontent.cgi?article=1990&context=etd default Graduate Theses and Dissertations Scholar Commons Praziquantel Ecteinascidin Isoquinolone Heterocycle Tetrahydroisoquinoline American Studies Arts and Humanities
collection	NDLTD
format	Others
sources	NDLTD
topic	Praziquantel Ecteinascidin Isoquinolone Heterocycle Tetrahydroisoquinoline American Studies Arts and Humanities
spellingShingle	Praziquantel Ecteinascidin Isoquinolone Heterocycle Tetrahydroisoquinoline American Studies Arts and Humanities Chen, Chiliu Efforts toward the First Enantioselective Total Synthesis of Praziquantel and Synthetic Model Studies on Ecteinascidin 743 by Novel Aromatic C-H Insertion Methodology
description	The thesis is composed of three chapters. The aim of this thesis is to apply the novel dirhodium perfluorobutyrate-catalyzed intramolecular aromatic C-H insertion methodology to the enantioselective total synthesis of praziquantel and synthetic model studies on ecteinascidin 743, which belongs to the important tetrahydroisoquinoline family. The first introductory chapter deals with the biological significance and previous synthetic methodologies. Our novel methodology is based on dirhodium perfluorobutyrate-catalyzed intromolecular aromatic C-H insertion reaction, which is crucial in the pivotal carbon-carbon bond formation when constructing isoquinolone moiety, which is ubiquitous in numerous natural products of significant biological and pharmacological activities. The second chapter takes on the first enantioselective total synthesis of praziquantel, an antihelmintic drug. Praziquantel is used worldwide to treat schistosomiasis, which has tremendous impact on the global fight on this disease affecting 150 million people. We believe this is the first asymmetric total synthesis to date, which is distinct from previous racemic syntheses reported. We also shed light on the mechanistic aspect of this key reaction to rationalize the superb regioselectivity and stereoselectivity achieved. The third chapter explores the synthetic model studies on ecteinascidin 743, a tetrahydroisoquinolone family natural product with significant antitumor and antimicrobial activities. Several different synthetic routes were attempted, including the N-Methyl and the N-Boc routes, and the results achieved contributed significantly to our final synthetic plan of the target molecule.
author	Chen, Chiliu
author_facet	Chen, Chiliu
author_sort	Chen, Chiliu
title	Efforts toward the First Enantioselective Total Synthesis of Praziquantel and Synthetic Model Studies on Ecteinascidin 743 by Novel Aromatic C-H Insertion Methodology
title_short	Efforts toward the First Enantioselective Total Synthesis of Praziquantel and Synthetic Model Studies on Ecteinascidin 743 by Novel Aromatic C-H Insertion Methodology
title_full	Efforts toward the First Enantioselective Total Synthesis of Praziquantel and Synthetic Model Studies on Ecteinascidin 743 by Novel Aromatic C-H Insertion Methodology
title_fullStr	Efforts toward the First Enantioselective Total Synthesis of Praziquantel and Synthetic Model Studies on Ecteinascidin 743 by Novel Aromatic C-H Insertion Methodology
title_full_unstemmed	Efforts toward the First Enantioselective Total Synthesis of Praziquantel and Synthetic Model Studies on Ecteinascidin 743 by Novel Aromatic C-H Insertion Methodology
title_sort	efforts toward the first enantioselective total synthesis of praziquantel and synthetic model studies on ecteinascidin 743 by novel aromatic c-h insertion methodology
publisher	Scholar Commons
publishDate	2004
url	https://scholarcommons.usf.edu/etd/991 https://scholarcommons.usf.edu/cgi/viewcontent.cgi?article=1990&context=etd
work_keys_str_mv	AT chenchiliu effortstowardthefirstenantioselectivetotalsynthesisofpraziquantelandsyntheticmodelstudiesonecteinascidin743bynovelaromaticchinsertionmethodology
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Efforts toward the First Enantioselective Total Synthesis of Praziquantel and Synthetic Model Studies on Ecteinascidin 743 by Novel Aromatic C-H Insertion Methodology

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