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Exploring the Chemoselective Transfo...

Lee, Chien-Hsun Frank.

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Exploring the Chemoselective Transformations of Boryl Carbonyls, Heterocycles, Peptide Macrocycles, and Boron Migration Processes.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Exploring the Chemoselective Transformations of Boryl Carbonyls, Heterocycles, Peptide Macrocycles, and Boron Migration Processes./
Author:	Lee, Chien-Hsun Frank.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2019,
Description:	396 p.
Notes:	Source: Dissertations Abstracts International, Volume: 80-10, Section: B.
Contained By:	Dissertations Abstracts International80-10B.
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10975524
ISBN:	9781392018194

Exploring the Chemoselective Transformations of Boryl Carbonyls, Heterocycles, Peptide Macrocycles, and Boron Migration Processes.
Lee, Chien-Hsun Frank.

Exploring the Chemoselective Transformations of Boryl Carbonyls, Heterocycles, Peptide Macrocycles, and Boron Migration Processes. - Ann Arbor : ProQuest Dissertations & Theses, 2019 - 396 p.

Source: Dissertations Abstracts International, Volume: 80-10, Section: B.

Thesis (Ph.D.)--University of Toronto (Canada), 2019.

This item must not be sold to any third party vendors.

Developing novel and efficient methods towards the synthesis of azacycles and macrocycles are subject to increased attention due to their applications in natural product synthesis and pharmaceutical drug design. This dissertation outlines the synthesis of borylated building blocks and heterocycles with applications in the discovery of bioactive molecules. This dissertation also documents the development of chemoselective syntheses of thioamide-containing macrocycles and novel boron transfer processes. An introduction to heterocyclic chemistry and boryl carbonyl molecules (Chapter 1) is followed by the synthetic and biological applications of novel borylated small molecules (Chapters 2-4). Chapter 2 details the synthetic applications of borylated enamines, enamides, and sulfamate esters. These boron-containing molecules were efficient in the synthesis and exploration of the B-C-N and B-C-C-N motifs towards borylated heterocycles such as thiazoles. The boryl enamides were also utilized as linchpin intermediates for the construction of polycyclic isoindolinone scaffolds. Chapter 3 documents the synthesis of bench-stable acyl boronates towards borylated thiazoles, imidazopyridines, and indolizines. These compounds mildly introduce the boronate moiety onto azacycles in a regioselective manner. The boronate group also provides a handle for the construction of boron-containing oxadiazaboroles and triazaboroles. Chapter 4 outlines the efficient synthesis of substituted oxalyl boronates and borylated imidazoles. The borylated imidazoles were subjected to optimized Suzuki-Miyaura cross-coupling conditions to complete a modular synthesis of 2,4,5-trisubstituted imidazoles. Select imidazole substrates were found to be potent chemical probes for the protein kinase STK10. Chapter 5 explores the potential chemoselective thionation of peptide macrocycles and the effect of thioamide incorporation to the peptide conformation through photochemistry. Preliminary results showed mixtures of mono- and di-thionated cyclic peptides and the photochemically-induced cyclization of thionated dipeptides to diketopiperazines. Finally, Chapter 6 delves into the experimental and computational efforts towards understanding the boron transfer reactions we observed in certain chemical systems. The hemilability of the ligand attached to boron mechanistically played a key role in boron acting like a proton or a hydride in certain transfer processes. Several novel boron migration reactions were developed based on mechanistic findings and will continue to prompt further synthetic applications of boron-containing molecules.

ISBN: 9781392018194Subjects--Topical Terms:

523952
Organic chemistry.

Exploring the Chemoselective Transformations of Boryl Carbonyls, Heterocycles, Peptide Macrocycles, and Boron Migration Processes.
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245 1 0 $a Exploring the Chemoselective Transformations of Boryl Carbonyls, Heterocycles, Peptide Macrocycles, and Boron Migration Processes.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2019
300 $a 396 p.
500 $a Source: Dissertations Abstracts International, Volume: 80-10, Section: B.
500 $a Publisher info.: Dissertation/Thesis.
500 $a Yudin, Andrei K.
502 $a Thesis (Ph.D.)--University of Toronto (Canada), 2019.
506 $a This item must not be sold to any third party vendors.
520 $a Developing novel and efficient methods towards the synthesis of azacycles and macrocycles are subject to increased attention due to their applications in natural product synthesis and pharmaceutical drug design. This dissertation outlines the synthesis of borylated building blocks and heterocycles with applications in the discovery of bioactive molecules. This dissertation also documents the development of chemoselective syntheses of thioamide-containing macrocycles and novel boron transfer processes. An introduction to heterocyclic chemistry and boryl carbonyl molecules (Chapter 1) is followed by the synthetic and biological applications of novel borylated small molecules (Chapters 2-4). Chapter 2 details the synthetic applications of borylated enamines, enamides, and sulfamate esters. These boron-containing molecules were efficient in the synthesis and exploration of the B-C-N and B-C-C-N motifs towards borylated heterocycles such as thiazoles. The boryl enamides were also utilized as linchpin intermediates for the construction of polycyclic isoindolinone scaffolds. Chapter 3 documents the synthesis of bench-stable acyl boronates towards borylated thiazoles, imidazopyridines, and indolizines. These compounds mildly introduce the boronate moiety onto azacycles in a regioselective manner. The boronate group also provides a handle for the construction of boron-containing oxadiazaboroles and triazaboroles. Chapter 4 outlines the efficient synthesis of substituted oxalyl boronates and borylated imidazoles. The borylated imidazoles were subjected to optimized Suzuki-Miyaura cross-coupling conditions to complete a modular synthesis of 2,4,5-trisubstituted imidazoles. Select imidazole substrates were found to be potent chemical probes for the protein kinase STK10. Chapter 5 explores the potential chemoselective thionation of peptide macrocycles and the effect of thioamide incorporation to the peptide conformation through photochemistry. Preliminary results showed mixtures of mono- and di-thionated cyclic peptides and the photochemically-induced cyclization of thionated dipeptides to diketopiperazines. Finally, Chapter 6 delves into the experimental and computational efforts towards understanding the boron transfer reactions we observed in certain chemical systems. The hemilability of the ligand attached to boron mechanistically played a key role in boron acting like a proton or a hydride in certain transfer processes. Several novel boron migration reactions were developed based on mechanistic findings and will continue to prompt further synthetic applications of boron-containing molecules.
590 $a School code: 0779.
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710 2 $a University of Toronto (Canada). $b Chemistry. $3 3178441
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