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Reimagining Molecular Disconnections : = Perspectives on Total Synthesis and Skeletal Editing.

紀錄類型:	書目-語言資料,手稿 : Monograph/item
正題名/作者:	Reimagining Molecular Disconnections :/
其他題名:	Perspectives on Total Synthesis and Skeletal Editing.
作者:	Falcone, Nicholas Angelo.
面頁冊數:	1 online resource (322 pages)
附註:	Source: Dissertations Abstracts International, Volume: 85-12, Section: B.
Contained By:	Dissertations Abstracts International85-12B.
標題:	Chemistry. -
電子資源:	click for full text (PQDT)
ISBN:	9798382811185

Reimagining Molecular Disconnections : = Perspectives on Total Synthesis and Skeletal Editing.
Falcone, Nicholas Angelo.

Reimagining Molecular Disconnections :Perspectives on Total Synthesis and Skeletal Editing. - 1 online resource (322 pages)

Source: Dissertations Abstracts International, Volume: 85-12, Section: B.

Thesis (Ph.D.)--Princeton University, 2024.

Includes bibliographical references

The natural product estate harbors a multitude of structurally diverse scaffolds that challenge the limits of modern synthetic methods. This has motivated the development of new strategies to effect challenging bond constructions and expand the scope of feasible retrosynthetic connections. Site-selective C-H functionalization has emerged as a powerful tactic for circumventing traditional obstacles in complex molecule synthesis. The first section of this work describes our efforts towards the synthesis of maoecrystal V, a historically formidable natural product with an unprecedented molecular framework. An intramolecular rhodium catalyzed C-H insertion facilitates the construction of an advanced tetracyclic intermediate, and we implement a topology-guided approach to establish an elusive quaternary center at the heart of the molecule. The second section describes an enantioselective synthesis of (-)-aflatoxin B2 that produces a key carbon−carbon bond, a benzylic stereocenter, and two arene carbon−oxygen bonds in the course of three C−H functionalizations-an asymmetric rhodium carbene C-H insertion and a palladium catalyzed bis-C(sp2)-H oxidation. Inspired by the diverse frameworks of natural products and the enabling potential of the site-selective peripheral functionalizations, we were drawn to the idea of editing the core skeletons of biologically and pharmaceutically relevant scaffolds, which culminated in a reaction capable of achieving N-to-C point mutations of azaarene N-oxides.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2024

Mode of access: World Wide Web

ISBN: 9798382811185Subjects--Topical Terms:

593913
Chemistry.
Subjects--Index Terms:

AflatoxinsIndex Terms--Genre/Form:

554714
Electronic books.

Reimagining Molecular Disconnections : = Perspectives on Total Synthesis and Skeletal Editing.
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520 $a The natural product estate harbors a multitude of structurally diverse scaffolds that challenge the limits of modern synthetic methods. This has motivated the development of new strategies to effect challenging bond constructions and expand the scope of feasible retrosynthetic connections. Site-selective C-H functionalization has emerged as a powerful tactic for circumventing traditional obstacles in complex molecule synthesis. The first section of this work describes our efforts towards the synthesis of maoecrystal V, a historically formidable natural product with an unprecedented molecular framework. An intramolecular rhodium catalyzed C-H insertion facilitates the construction of an advanced tetracyclic intermediate, and we implement a topology-guided approach to establish an elusive quaternary center at the heart of the molecule. The second section describes an enantioselective synthesis of (-)-aflatoxin B2 that produces a key carbon−carbon bond, a benzylic stereocenter, and two arene carbon−oxygen bonds in the course of three C−H functionalizations-an asymmetric rhodium carbene C-H insertion and a palladium catalyzed bis-C(sp2)-H oxidation. Inspired by the diverse frameworks of natural products and the enabling potential of the site-selective peripheral functionalizations, we were drawn to the idea of editing the core skeletons of biologically and pharmaceutically relevant scaffolds, which culminated in a reaction capable of achieving N-to-C point mutations of azaarene N-oxides.
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