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Discovery and Development of a Three-Component Oxidopyrylium Cycloaddition and Its Application towards alpha-Hydroxytropolone Synthesis.

Record Type:	Language materials, manuscript : Monograph/item
Title/Author:	Discovery and Development of a Three-Component Oxidopyrylium Cycloaddition and Its Application towards alpha-Hydroxytropolone Synthesis./
Author:	D'Erasmo, Michael P.
Description:	1 online resource (293 pages)
Notes:	Source: Dissertation Abstracts International, Volume: 79-07(E), Section: B.
Contained By:	Dissertation Abstracts International79-07B(E).
Subject:	Organic chemistry. -
Online resource:	click for full text (PQDT)
ISBN:	9780355636963

Discovery and Development of a Three-Component Oxidopyrylium Cycloaddition and Its Application towards alpha-Hydroxytropolone Synthesis.
D'Erasmo, Michael P.

Discovery and Development of a Three-Component Oxidopyrylium Cycloaddition and Its Application towards alpha-Hydroxytropolone Synthesis. - 1 online resource (293 pages)

Source: Dissertation Abstracts International, Volume: 79-07(E), Section: B.

Thesis (Ph.D.)--City University of New York, 2018.

Includes bibliographical references

Historically, natural products have provided unique research opportunities and challenges for organic synthesis, chemical biology, and medicinal chemistry due to their molecular complexity and effects on physiological systems. The total synthesis of natural products has not only produced novel reaction methods and strategies capable of efficiently generating complex structural motifs but also granted access to sufficient quantities of otherwise scarce natural product material for clinical evaluation. These synthetic efforts have facilitated the formation of a transdisciplinary partnership between chemistry, biology, and medicine that has been paramount in elucidating the chemical and pharmaceutical utility of natural products. Chapter I of this thesis will highlight several key examples of how natural products inspired synthetic methodology, small molecule drug and probe development, and the discovery of previously unknown biologically active scaffolds. A particular focus will be spent on the synthetic and biological endeavors made by our laboratory involving alpha-hydroxytropolones (alphaHTs).

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2018

Mode of access: World Wide Web

ISBN: 9780355636963Subjects--Topical Terms:

1148722
Organic chemistry.
Index Terms--Genre/Form:

554714
Electronic books.

Discovery and Development of a Three-Component Oxidopyrylium Cycloaddition and Its Application towards alpha-Hydroxytropolone Synthesis.
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245 1 0 $a Discovery and Development of a Three-Component Oxidopyrylium Cycloaddition and Its Application towards alpha-Hydroxytropolone Synthesis.
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300 $a 1 online resource (293 pages)
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500 $a Source: Dissertation Abstracts International, Volume: 79-07(E), Section: B.
500 $a Adviser: Ryan P. Murelli.
502 $a Thesis (Ph.D.)--City University of New York, 2018.
504 $a Includes bibliographical references
520 $a Historically, natural products have provided unique research opportunities and challenges for organic synthesis, chemical biology, and medicinal chemistry due to their molecular complexity and effects on physiological systems. The total synthesis of natural products has not only produced novel reaction methods and strategies capable of efficiently generating complex structural motifs but also granted access to sufficient quantities of otherwise scarce natural product material for clinical evaluation. These synthetic efforts have facilitated the formation of a transdisciplinary partnership between chemistry, biology, and medicine that has been paramount in elucidating the chemical and pharmaceutical utility of natural products. Chapter I of this thesis will highlight several key examples of how natural products inspired synthetic methodology, small molecule drug and probe development, and the discovery of previously unknown biologically active scaffolds. A particular focus will be spent on the synthetic and biological endeavors made by our laboratory involving alpha-hydroxytropolones (alphaHTs).
520 $a alphaHTs are a subclass of troponoid natural products that possess promising activity against a broad range of therapeutically significant targets. In order to gain access to these molecules, our laboratory utilizes an oxidopyrylium cycloaddition/ring-opening strategy. During our synthetic investigations, we recently discovered a three-component oxidopyrylium cycloaddition that generates novel 8-oxabicyclo[3,2,1]octene products. In Chapter II, the development and optimization of this synthetic method towards the construction of a library of new oxabicyclic species will be detailed. Initial attempts at applying the reaction towards alphaHT synthesis will also be discussed, as a tandem debenzylation/ring-opening procedure with benzyl-derived oxabicyclic intermediates is outlined. Further exploration of the utility of the three-component oxidopyrylium cycloaddition will be described in Chapter III and Chapter IV, as the first solid-phase and fluorous syntheses of alphaHTs are reported, respectively. The advantages and disadvantages of each strategy will be considered in these chapters, specifically pertaining to the efficiency of purification, incorporation/cleavage of solid-phase resins and fluorous tags, and modification of supported intermediates.
533 $a Electronic reproduction. $b Ann Arbor, Mich. : $c ProQuest, $d 2018
538 $a Mode of access: World Wide Web
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