Complexity Generating Annulation Reactions In The Synthesis Of Natural Products And Materials Scaffolds
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Complexity Generating Annulation Reactions In The Synthesis Of Natural Products And Materials Scaffolds
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Author : Robert Bergstrand Susick
language : en
Publisher:
Release Date : 2020
Complexity Generating Annulation Reactions In The Synthesis Of Natural Products And Materials Scaffolds written by Robert Bergstrand Susick and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 2020 with categories.
This dissertation encompasses several studies pertaining to natural product total synthesis, reaction methodology development, and organic materials. Given that natural product structures inspire the development of new agrochemicals and pharmaceuticals, their syntheses remain a worthwhile pursuit in organic chemistry. Furthermore, the successful completion of a total synthesis endeavor can confirm proposed molecular structures and biological activities, in addition to serving as a testing ground for new synthetic methods. Similarly, organic materials impact many areas of humanity, including technology, health, and energy conversion. Therefore, developing new reaction methodologies is crucial for expanding the architectures, and thereby properties, of organic materials. Specifically, photocatalysts and organic light-emitting diodes (OLEDs) often rely on photophysical properties imparted by N-containing polycyclic aromatic hydrocarbon (PAH) ligands. As such, new methods that provide access to unique N-containing heterocyclic scaffolds are highly desirable. Chapter one offers a current perspective on the field of natural product total synthesis. Although historically viewed as a highly competitive field, several recent syntheses demonstrate a growing spirit of collaboration in total synthesis. By forming alliances with chemists in other fields, industries, or laboratories, total synthesis chemists have made many breakthroughs that would arguably not have been possible if working independently. Chapter two describes our laboratory's total syntheses of several bioactive akuammiline alkaloids, including strictamine, 2(S)-cathafoline, akuammiline, -akuammigine, and 10-demethoxyvincorine. Our strategic approach to the natural products focused on the use of a modern variant of a classic reaction, the Fischer indolization, to install several rings and the common quaternary center found in each target. This strategy allowed for the first total syntheses of akuammilines bearing a methanoquinolizidine core, as well as those that bear vicinal quaternary centers. In addition, rearrangements of the methanoquinolizidine core were developed that allowed us to access pyrrolidinoindoline-containing akuammilines. Chapter three describes synthetic studies of the reactive intermediates 2,3-pyridyne and 4,5-pyrimidyne. Heterocycles bearing one or more nitrogen atom are privileged motifs in natural products and pharmaceuticals. Therefore, methodologies that decorate such heterocycles are of great interest to the synthetic and biological communities. Arynes are highly reactive, transient species that can efficiently build multiple bonds in a single transformation, and our lab is particularly interested in accessing new, heterocyclic arynes to study their reactivity. This study demonstrates the synthetic utility of 2,3-pyridyne and the undesired reactivity of a 4,5-pyrimidyne precursor. Chapter four describes synthetic studies toward the development of new methods to manipulate polypyridyl organometallic scaffolds. Ruthenium- and iridium-based polypyridyl organometallic complexes have been known for nearly a century and have broadly impacted the scientific community, including the areas of catalysis, bioimaging, and energy conversion. Despite decades of study, methods to synthesize polypyridyl ligands are limited to relatively few transformations, particularly when extending -conjugation. We detail the use of arynes to extend the conjugation of polypyridyl ligands "on-the-complex," thereby overcoming traditional limitations in ligand synthesis. We also disclose the first generation and trapping of a ligand-bound aryne on an organometallic complex. Chapter five describes the synthesis of a novel -extended carbazole ligand for the study of structure-property relationships in two-coordinate metal complexes. Recently, linear two-coordinate metal complexes of the general structure donor-metal-acceptor have been identified as promising dopants for OLEDs. Both the donor and acceptor ligand play a crucial role in tuning the photophysical properties of these complexes. However, donor ligands with extended -conjugation have not been studied in this context. Our approach leverages heterocyclic arynes to synthesize -extended donor ligands in a modular fashion, which can also apply to other PAHs. Subsequent photophysical studies of -extended two-coordinate metal complexes identify a new dopant that displays up to 80% photoluminescence efficiency.
Total Synthesis Of Natural Products
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Author : Jie Jack Li
language : en
Publisher: Springer Science & Business Media
Release Date : 2013-03-14
Total Synthesis Of Natural Products written by Jie Jack Li and has been published by Springer Science & Business Media this book supported file pdf, txt, epub, kindle and other format this book has been release on 2013-03-14 with Science categories.
'Total Synthesis of Natural Products' is written and edited by some of today's leaders in organic chemistry. Eleven chapters cover a range of natural products, from steroids to alkaloids. Each chapter contains an introduction to the natural product in question, descriptions of its biological and pharmacological properties and outlines of total synthesis procedures already carried out. Particular emphasis is placed on novel methodologies developed by the respective authors and their research groups. This text is ideal for graduate and advanced undergraduate students, as well as organic chemists in academia and industry.
Organic Syntheses Collective Volume 12
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Author : Charles K. Zercher
language : en
Publisher: John Wiley & Sons
Release Date : 2015-10-19
Organic Syntheses Collective Volume 12 written by Charles K. Zercher and has been published by John Wiley & Sons this book supported file pdf, txt, epub, kindle and other format this book has been release on 2015-10-19 with Science categories.
Continuing the tradition of providing significant and interesting procedures, Organic Syntheses, Collective Volume XII is a compilation of revised editions of Annual Volumes 85 through 89. The contents of this volume are organized by primarily by reaction type, with the precise classification made according to the bias of the editor, who attempted to ascertain the primary purpose or utility of the procedure.
Synthesis And Reactivity Of Donor Acceptor Substituted Aminocyclopropanes And Aminocyclobutanes
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Author : Florian de Nanteuil
language : en
Publisher: Springer
Release Date : 2015-09-26
Synthesis And Reactivity Of Donor Acceptor Substituted Aminocyclopropanes And Aminocyclobutanes written by Florian de Nanteuil and has been published by Springer this book supported file pdf, txt, epub, kindle and other format this book has been release on 2015-09-26 with Science categories.
This thesis presents a general approach to accessing nitrogen-substituted hetero- and carbocycles. In short, the annulation reactions developed in the thesis make it possible to access nitrogen-substituted four-, five- and six-membered rings, all essential building blocks for the synthesis of bioactive molecules. Many natural products display a saturated polycyclic core allowing a well-defined arrangement of functional groups in space. As such, they can interact with biological targets with a high degree of affinity and selectivity, surpassing many synthetic drugs. Nevertheless, the efficient synthesis of such complex ring systems poses a challenge for organic chemistry. Through careful tuning of the electronic properties of a nitrogen donor group and a diester acceptor group, the first [3+2] annulation reaction between aminocyclopropanes and enol ethers or carbonyl compounds is now possible. The reaction proceeded under mild catalytic conditions, and the building blocks obtained can be found at the core of bioactive alkaloids, drugs such as Ramipril and biomolecules such as DNA and RNA. Thanks to the dynamic kinetic asymmetric annulation of aminocyclopropanes with enol ethers and aldehydes, access to enantioenriched compounds is also now possible. Lastly, a synthesis of donor-acceptor aminocyclobutanes via [2+2] cycloaddition using a cheap iron catalyst was developed, allowing them to be used in [4+2] annulations to access cyclohexylamines.
Recent Advances In Organocatalytic Cascade Reactions For Enantioselective Synthesis Of Chiral Spirolactone Skeletons
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Author : Jun Yang
language : en
Publisher: OAE Publishing Inc.
Release Date : 2023-02-08
Recent Advances In Organocatalytic Cascade Reactions For Enantioselective Synthesis Of Chiral Spirolactone Skeletons written by Jun Yang and has been published by OAE Publishing Inc. this book supported file pdf, txt, epub, kindle and other format this book has been release on 2023-02-08 with Science categories.
Chiral spirolactones, including spiropropyllactones, spirobutyrolactones, and spirovalerolactones, are important heterocyclic frameworks that attracted the attention of organic and medicinal chemists because these motifs constitute the core structure of several natural products and bioactive molecules. The absolute configuration and the substituents on the fully substituted spirocyclic stereocenter of the lactone can potentially enhance specificity for ligand-protein binding and enhance bioavailability, potency, and metabolic stability. So, intensive attention from chemists has been paid to the synthetic methods leading to such prominent structural motifs. The synthetic methods can be divided into two main classes. The first approach takes advantage of the presence of the existing lactone structure and focuses on its functionalization. The second approach is the lactone framework constructed from various precursors in a direct spirolactonization reaction. In this review, for convenience in reading, the recent advances in the synthesis of spirolactones are summarized and discussed according to the two major organocatalytic asymmetric synthetic routes: (i) using the lactone-related frameworks as building blocks; and (ii) direct spirolactonization reaction using various reagents. This review also describes both the mechanisms and related transformations, and gives some insights into challenging issues in this research field, which will enlighten the future development of this field.
The Pauson Khand Reaction
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Author : Ramon Rios Torres
language : en
Publisher: John Wiley & Sons
Release Date : 2012-03-01
The Pauson Khand Reaction written by Ramon Rios Torres and has been published by John Wiley & Sons this book supported file pdf, txt, epub, kindle and other format this book has been release on 2012-03-01 with Science categories.
The Pauson-Khand reaction is an important reaction in the field of organic chemistry. It involves the transition-metal catalysed cycloaddition of an alkyne, an alkene and carbon monoxide, to produce cyclopentenones. The importance of this reaction originates from its high value in transforming simple components into the synthetically useful cyclopentenone unit, in which a high degree of molecular complexity can be achieved in a single step, with impressive stereochemical and regiochemical control. The Pauson-Khand Reaction investigates the nature and many variations of this reaction. Topics covered include: the mechanisms of Pauson‐Khand-type reactions non chiral intramolecular and intermolecular versions of Pauson‐Khand reactions asymmetric Pauson‐Khand reaction using chiral auxiliaries the enantioselective Pauson‐Khand reaction Pauson‐Khand reactions catalysed by metals other than cobalt unconventional Pauson‐Khand reactions the Pauson‐Khand reaction in total synthesis Presenting a comprehensive overview of this fundamental reaction, The Pauson-Khand Reaction will find a place on the bookshelves of any organic or organometallic chemist.
Bioactive Heterocyclic Compound Classes
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Author : Clemens Lamberth
language : en
Publisher: John Wiley & Sons
Release Date : 2012-08-16
Bioactive Heterocyclic Compound Classes written by Clemens Lamberth and has been published by John Wiley & Sons this book supported file pdf, txt, epub, kindle and other format this book has been release on 2012-08-16 with Science categories.
The chemistry of heterocycles is an important branch of organic chemistry. This is due to the fact that a large number of natural products, e. g. hormones, antibiotics, vitamins, etc. are composed of heterocyclic structures. Often, these compounds show beneficial properties and are therefore applied as pharmaceuticals to treat diseases or as insecticides, herbicides or fungicides in crop protection. This volume presents important pharmaceuticals. Each of the 20 chapters covers in a concise manner one class of heterocycles, clearly structuredas follows: * Structural formulas of most important examples (market products) * Short background of history or discovery * Typical syntheses of important examples * Mode of action * Characteristic biological activity * Structure-activity relationship * Additional chemistry information (e.g. further transformations, alternative syntheses, metabolic pathways, etc.) * References. A valuable one-stop reference source for researchers in academia and industry as well as for graduate students with career aspirations in the pharmaceutical chemistry.
Organic Reaction Mechanisms 2020
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Author : Mark G. Moloney
language : en
Publisher: John Wiley & Sons
Release Date : 2024-03-08
Organic Reaction Mechanisms 2020 written by Mark G. Moloney and has been published by John Wiley & Sons this book supported file pdf, txt, epub, kindle and other format this book has been release on 2024-03-08 with Science categories.
Organic Reaction Mechanisms 2020, the 56th annual volume in this highly successful and unique series, surveys research on organic reaction mechanisms described in the available literature dated 2020. The following classes of organic reaction mechanisms are comprehensively reviewed: Reaction of Aldehydes and Ketones and their Derivatives Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives Oxidation and Reduction Nucleophilic Aromatic Substitution Electrophilic Aromatic Substitution Carbocations Nucleophilic Aliphatic Substitution Carbanions and Electrophilic Aliphatic Substitution Elimination Reactions Polar Addition Reactions Cycloaddition Reactions Molecular Rearrangements Transition Metal Coupling Radicals An experienced team of authors compile these reviews every year, so that the reader can rely on a continuing quality of selection and presentation.
Green Techniques For Organic Synthesis And Medicinal Chemistry
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Author : Wei Zhang
language : en
Publisher: John Wiley & Sons
Release Date : 2018-03-19
Green Techniques For Organic Synthesis And Medicinal Chemistry written by Wei Zhang and has been published by John Wiley & Sons this book supported file pdf, txt, epub, kindle and other format this book has been release on 2018-03-19 with Science categories.
An updated overview of the rapidly developing field of green techniques for organic synthesis and medicinal chemistry Green chemistry remains a high priority in modern organic synthesis and pharmaceutical R&D, with important environmental and economic implications. This book presents comprehensive coverage of green chemistry techniques for organic and medicinal chemistry applications, summarizing the available new technologies, analyzing each technique’s features and green chemistry characteristics, and providing examples to demonstrate applications for green organic synthesis and medicinal chemistry. The extensively revised edition of Green Techniques for Organic Synthesis and Medicinal Chemistry includes 7 entirely new chapters on topics including green chemistry and innovation, green chemistry metrics, green chemistry and biological drugs, and the business case for green chemistry in the generic pharmaceutical industry. It is divided into 4 parts. The first part introduces readers to the concepts of green chemistry and green engineering, global environmental regulations, green analytical chemistry, green solvents, and green chemistry metrics. The other three sections cover green catalysis, green synthetic techniques, and green techniques and strategies in the pharmaceutical industry. Includes more than 30% new and updated material—plus seven brand new chapters Edited by highly regarded experts in the field (Berkeley Cue is one of the fathers of Green Chemistry in Pharma) with backgrounds in academia and industry Brings together a team of international authors from academia, industry, government agencies, and consultancies (including John Warner, one of the founders of the field of Green Chemistry) Green Techniques for Organic Synthesis and Medicinal Chemistry, Second Edition is an essential resource on green chemistry technologies for academic researchers, R&D professionals, and students working in organic chemistry and medicinal chemistry.
Anionic Annulations In Organic Synthesis
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Author : Dipakranjan Mal
language : en
Publisher: Elsevier
Release Date : 2018-10-25
Anionic Annulations In Organic Synthesis written by Dipakranjan Mal and has been published by Elsevier this book supported file pdf, txt, epub, kindle and other format this book has been release on 2018-10-25 with Science categories.
Anionic Annulations in Organic Synthesis: A Versatile and Prolific Class of Ring-Forming Reactions is a comprehensive review of the best annulations for the construction of cyclic structures and their applications in the total synthesis of functional molecules. The reactions described in the work are particularly useful for the synthesis of polyoxygenated polycyclic compounds, including tetracyclines, angucyclines, uncialamycins, and lignans, among other compounds. Included in detail are the Hauser, Robinson, Sammes and Meyers annulations, all of which can be effectively used to construct substrates with complex molecular structures. This work provides the tools to master anionic organic chemistry, ortho-lithiation, lateral lithaition/metalation and organic selectivity issues, like chemoselectivity, regioselectivity and stereoselectivity. This book is a valuable resource for organic chemists, researchers and students seeking a complete and detailed understanding of anionic annulations. Provides a comprehensive review of anionic cyclization for chemical construction of a variety of cyclic scaffolds involved in many kinds of biologically active natural products and pharmaceutical drugs Serves as a useful tool to academic and industrial researchers working on the synthesis of cyclic compounds as their targets Includes many examples of anionic annulations and practical information on how to use them in research and industry Features anionic annulations that are particularly useful for the synthesis of polyoxygenated polycyclic compounds, including tetracyclines, angucyclines, uncialamycins and lignans