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Total Synthesis Of N Methylwelwitindolinone B Isothiocyanate And Nickel Catalyzed Reactions Of Amide Derivatives
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Book Synopsis Total Synthesis of N-Methylwelwitindolinone B Isothiocyanate and Nickel-Catalyzed Reactions of Amide Derivatives by : Emma Lee Baker-Tripp
Download or read book Total Synthesis of N-Methylwelwitindolinone B Isothiocyanate and Nickel-Catalyzed Reactions of Amide Derivatives written by Emma Lee Baker-Tripp and published by . This book was released on 2018 with total page 722 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation describes our efforts toward the total synthesis of N-methyl welwitindolinone B isothioscyanate, as well as the development of reactions involving the nickel-catalyzed activation of amide C-N bonds. The welwitindolinones have been long-standing targets in total synthesis for over two decades due to their complex structures and interesting biological profiles. This dissertation describes the completed total synthesis of a particularly challenging family member, N-methylwelwitindolinone B isothiocyanate. Moreover, several nickel-catalyzed transformations of amides are described each showcasing the unique reactivity of this non-precious metal and highlighting the utility of amides, once considered inert substrates, as useful synthons in organic synthesis. Chapter one describes our enantiospecific total synthesis of N-methylwelwitindolinone B isothiocyanate. Our approach to the natural product features an aryne cyclization to construct the bicyclo[4.3.1]decane core of the molecule, as well as a C-H nitrene insertion reaction to introduce the bridgehead nitrogen substituent. The key step involving a regio- and diastereoselective chlorinative oxabicycle opening is detailed, which enables the first total synthesis of N-methylwelwitindolinone B isothiocyanate. Chapters two and three describe the development of nickel-catalyzed esterification reactions of amides. Chapter two showcases the first nickel-catalyzed activation of amides in an esterification of benzamides. This study suggests that amides could serve to be useful synthetic building blocks in a variety of cross-coupling reactions. Chapter three builds upon the previous study to expand the scope to include the activation of amides derived from aliphatic carboxylic acids. Chapters four and five describe the development of nickel-catalyzed C-N bond-forming reactions of amides. More specifically, chapters four and five outline the transamidation reaction of aromatic and aliphatic amides, respectively. These methodologies utilize a two-step approach to enable the transamidation of secondary amides. These two methods address the long-standing challenge of secondary amide transamidation. Chapter six describes the development of a nickel-catalyzed C-C bond-forming reaction of amides. The first nickel-catalyzed Suzuki-Miyaura coupling of aromatic amides is disclosed and provides a new and mild method for ketone synthesis. This study demonstrates that amides can now be utilized as synthons for use in C-C bond forming reactions through cleavage of the amide C-N bond.
Book Synopsis Total Synthesis of Welwitindolinones and Nickel-Catalyzed Reactions of Amide Derivatives by : Nicholas Anthony Weires
Download or read book Total Synthesis of Welwitindolinones and Nickel-Catalyzed Reactions of Amide Derivatives written by Nicholas Anthony Weires and published by . This book was released on 2017 with total page 560 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation describes our efforts toward the total synthesis of welwitindolinone natural products, as well as the development of reactions involving the nickel-catalyzed activation of amide C-N bonds. The welwitindolinones have been long-standing targets in total synthesis for over two decades, and this dissertation describes two completed total syntheses of these alkaloids. In addition, several nickel-catalyzed transformations of amides are outlined, each of which demonstrate the powerful reactivity of nickel and highlight the utility of amides as synthetic building blocks. Chapters one and two present our enantiospecific total syntheses of the welwitindolinone alkaloids N-methylwelwitindolinone D isonitrile and N-methylwelwitindolinone B isothiocyanate. Our approach to these natural products features an aryne cyclization to construct the bicyclo[4.3.1]decane core of the molecules, as well as a C-H nitrene insertion reaction to introduce the bridgehead nitrogen substituent. In chapter one, a dual C-H functionalization event installs the challenging ether linkage and allows for completion of (-)-N-methylwelwitindolinone D isonitrile. In chapter two, a regio- and diastereoselective chlorinative oxabicyclic opening is detailed, which enables the first total synthesis of N-methylwelwitindolinone B isothiocyanate. Chapters three, four, and five describe the development of nickel-catalyzed carbon-carbon bond-forming reactions of amides. More specifically, chapters three and four outline the Suzuki-Miyaura couplings of aromatic and aliphatic amides, respectively, whereas chapter five details the alkylation of amide derivatives. These methodologies represent mild and complementary tools to the Weinreb ketone synthesis, proceeding through the nickel-catalyzed activation of the amide C-N bond. It is shown that amides, which were traditionally thought of as inert functionalities, can be utilized as synthons in C-C bond-forming reactions. Chapter six describes a method for the benchtop delivery of Ni(cod)2 involving the encapsulation of Ni(cod)2 in paraffin wax. Due to air- and moisture-sensitivity, Ni(cod)2 is normally handled under an inert atmosphere. Using our method of wax encapsulation, several nickel-catalyzed transformations are performed without the use of a glove box, including various amide C-N bond cleavage reactions. These studies are aimed at promoting the widespread use of nickel in transition metal catalysis. Chapter seven illustrates the kinetic modeling of the nickel-catalyzed esterification of amides. By developing a kinetic model, an optimization is undertaken that allows for the employment of catalyst loadings as low as 0.4 mol% nickel. This demonstration is intended to foster the advancement of kinetic modeling as a powerful tool in methodology development.
Book Synopsis Progress Toward the Total Synthesis of N-Methylwelwitindolinone C Isothiocyanate by : Jibo Xia
Download or read book Progress Toward the Total Synthesis of N-Methylwelwitindolinone C Isothiocyanate written by Jibo Xia and published by . This book was released on 2007 with total page 680 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies Towards the Total Synthesis of N-methylwelwitindolinone C Isothiocyanate by : Bick Vivant
Download or read book Studies Towards the Total Synthesis of N-methylwelwitindolinone C Isothiocyanate written by Bick Vivant and published by . This book was released on 2012 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: N-Methylwelwitindolinone C isothiocyanate (7), isolated from the blue green algae Hapalosiphon welwitschii and Westiella intricate, is a structurally novel alkaloid related to the welwitindolinone family. This thesis describes studies towards the total synthesis of this natural product. Chapter One introduces the biological activities and the proposed biosyntheses of the welwitindolinone alkaloids. The synthetic studies towards the synthesis of this class of natural products will be also discussed. Chapter Two describes the different strategies towards the synthesis of a bicyclo[4.3.1]decane scaffold possessing a gem-dimethyl group present in the natural product 7. The geminal group was envisioned via a methyl addition to a carbonyl, a deprotonation of a sulfone or an intramolecular Michael addition. Generation of the desired skeleton 182 was achieved by using an intramolecular palladium-catalysed [alpha]-arylation of a trimethylsilyl enol ether. Chapter Three describes various attempts to the direct installation of a nitrogen functionality at the bridgehead position. In an indirect mode, a regioselective deprotonation allowed functionalisation of the desired bridgehead position and the access to isocyanate 297 and diketoazide 276, respectively obtained from a [3,3]-sigmatropic rearrangement and an aza- Michael reaction. A three step sequence involving a regioselective deprotonation of diketoazide 276, followed by aldol condensation and dehydration led to the advance intermediate 306. Chapter Four describes the recent breakthrough in the synthesis of the welwitindolinone alkaloids. The total synthesis of N-methylwelwitindolinone D isonitrile (19) and N-methylwelwitindolinone C isothiocyanate (7), along with related studies reported this year. Chapter Five includes the experimental procedures and analytical data for the preparation of novel compounds described during the course of this study.
Book Synopsis Progress Toward the Total Synthesis of N-methylwelwitindolinone C Isothiocyanate by : Hongbo Deng
Download or read book Progress Toward the Total Synthesis of N-methylwelwitindolinone C Isothiocyanate written by Hongbo Deng and published by . This book was released on 2001 with total page 508 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Progress towards the total synthesis of n-methylwelwitindolinone c isothiocyanate by : Valerie Beatrice Sylvie Boissel
Download or read book Progress towards the total synthesis of n-methylwelwitindolinone c isothiocyanate written by Valerie Beatrice Sylvie Boissel and published by . This book was released on 2009 with total page 273 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Progress Towards the Total Synthesis of N-methylwelwitindolinone C Isothiocyanate by : Cynthia Béatrice Julie Paulin
Download or read book Progress Towards the Total Synthesis of N-methylwelwitindolinone C Isothiocyanate written by Cynthia Béatrice Julie Paulin and published by . This book was released on 2013 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: This thesis focuses on our progress towards the total synthesis of N-methylwelwitindolinone C isothiocyanate 7, commonly called welwistatin. This major alkaloid of the welwitindolinone family, which was isolated from Hapalosiphon welwitschii in 1994, represents a particularly attractive target due to its interesting biological activities (MDR reversing agent) and its challenging structure. Welwistatin possesses a complex bicyclo[4.3.1]decane ring system consisting of four stereogenic centres, three quaternary carbons and two unusual reactive functionalities: the isothiocyanate bridgehead and a vinyl chloride group. Inspired by the synthetic challenge of this complex architecture, the Simpkins group reported an expedient four-step synthesis of its core structure in 2005. Three years later, our group had investigated the reactivity at the bridgehead enolate positions. Taking inspiration from this previous work, we successfully synthesised bridgehead alkene 126. The other features present on welwistatin 7 were then investigated and enone 198 was obtained. Facing some difficulties on the model system 88, we turned our attention towards the synthesis of tetracycle 170, possessing the gem-dimethyl at the position C\(_{16}\), and its subsequent functionalisation.
Book Synopsis Cascade Biocatalysis by : Sergio Riva
Download or read book Cascade Biocatalysis written by Sergio Riva and published by John Wiley & Sons. This book was released on 2014-06-23 with total page 587 pages. Available in PDF, EPUB and Kindle. Book excerpt: This ready reference presents environmentally friendly and stereoselective methods of modern biocatalysis. The experienced and renowned team of editors have gathered top international authors for this book. They cover such emerging topics as chemoenzymatic methods and multistep enzymatic reactions, while showing how these novel methods and concepts can be used for practical applications. Multidisciplinary topics, including directed evolution, dynamic kinetic resolution, and continuous-flow methodology are also discussed. From the contents: * Directed Evolution of Ligninolytic Oxidoreductases: from Functional Expression to Stabilization and Beyond * New Trends in the In Situ Enzymatic Recycling of NAD(P)(H) Cofactors * Monooxygenase-Catalyzed Redox Cascade Biotransformations * Biocatalytic Redox Cascades Involving w-Transaminases * Multi-Enzyme Systems and Cascade Reactions Involving Cytochrome P450 Monooxygenases * Chemo-Enzymatic Cascade Reactions for the Synthesis of Glycoconjugates * Synergies of Chemistry and Biochemistry for the Production of Beta-Amino Acids * Racemizable Acyl Donors for Enzymatic Dynamic Kinetic Resolution * Stereoselective Hydrolase-Catalyzed Processes in Continuous-Flow Mode * Perspectives on Multienzyme Process Technology * Nitrile Converting Enzymes Involved in Natural and Synthetic Cascade Reactions * Mining Genomes for Nitrilases * Key-Study on the Kinetic Aspects of the In-Situ NHase/AMase Cascade System of M. imperiale Resting Cells for Nitrile Bioconversion * Enzymatic Stereoselective Synthesis of Beta-Amino Acids * New Applications of Transketolase: Cascade Reactions for Assay Development * Aldolases as Catalyst for the Synthesis of Carbohydrates and Analogs * Enzymatic Generation of Sialoconjugate Diversity * Methyltransferases in Biocatalysis * Chemoenzymatic Multistep One-Pot Processes
Book Synopsis Main Group Metals in Organic Synthesis by : Hisashi Yamamoto
Download or read book Main Group Metals in Organic Synthesis written by Hisashi Yamamoto and published by John Wiley & Sons. This book was released on 2006-03-06 with total page 905 pages. Available in PDF, EPUB and Kindle. Book excerpt: This is the first handbook to cover in detail all aspects of this fascinating field of chemistry. In this handy two-volume set, readers will instantly find the information they need, clearly structured according to the individual metals in the main groups, hitherto only accessible after much time-consuming research. The result is in indispensable aid for everyday work in the lab. Alongside all the classical organic reactions, this book focuses on the modern variations as well as novel, current reactions in organic synthesis that are closely linked to main group elements - both stoechiometric and catalytic. With this work the two prizewinning editors have succeeded in producing a comprehensive compendium of the main group metals as reagents for organic reactions. In short, this is a must for every organic chemist, whether as an efficient introduction to current research, for retaining an overview or for looking up detailed information.
Book Synopsis Modern Aryne Chemistry by : Akkattu T. Biju
Download or read book Modern Aryne Chemistry written by Akkattu T. Biju and published by John Wiley & Sons. This book was released on 2021-08-23 with total page 530 pages. Available in PDF, EPUB and Kindle. Book excerpt: A groundbreaking book to offer a a comprehensive account of important reactions involving arynes Modern Aryne Chemistry is the first book on the market to offer a conceptual framework to the reactions related to arynes. It also provides a systematic introduction to the cycloaddition reactions, insertion reactions and transition-metal-catalyzed transformations of arynes. The author, a noted expert on the topic, highlights a novel strategy for carbon-carbon and carbon-heteroatom bond construction using arynes. The book reveiws the recent use of aryne chemistry for the development of new multicomponent reactions. New advances in this area has shown rapid emergence of a new class of reactions classified under rearrangement reactions. The author also includes information on aryne methods that have been employed for the synthesis of several natural products. The simplicity and sophistication of the synthetic strategy using arynes can serve as a springboard for organic chemists to explore new possibilities and imagine applications of the concept of arynes. This important book: Presents a one-of-kind comprehensive guide to arynes reactions Offers a proven approach to the synthesis of natural product and polymers Reviews the most recent developments in the carbon-carbon and carbon-heteroatom bond-forming reactions involving arynes Written for organic, pharmaceutical, medicinal, natural products, and catalytic Chemists, Modern Aryne Chemistry offers a comprehensive review of the fundamentals of reactions related to arynes and the most recent developments in the field.
Book Synopsis Silver Catalysis in Organic Synthesis by : Chao-Jun Li
Download or read book Silver Catalysis in Organic Synthesis written by Chao-Jun Li and published by John Wiley & Sons. This book was released on 2018-12-07 with total page 400 pages. Available in PDF, EPUB and Kindle. Book excerpt: Covers all the aspects of the recent achievements in silver catalyzed reactions Silver catalysis has emerged as a powerful tool in the field of organic synthesis. This comprehensive book systematically explores the unique performance of silver catalysis, introducing all the recent progress of silver catalysis in organic synthesis. It clearly emphasizes the unique features of silver catalysis and provides the reaction mechanism involved. This two-volume book also provides vivid schematics and tables throughout to enhance the accessibility to the relevant theory and mechanisms. Silver Catalysis in Organic Synthesis begins with an introduction to Silver Chemistry before moving on to chapters covering: Silver-Catalyzed Cycloaddition Reactions; Silver-Catalyzed Cyclizations; Silver-Mediated Radical Reactions; Silver-Mediated Fluorination, Perfluoroalkylation and Trifluoromethylthiolation Reactions; Coupling Reactions and C-H Functionalization; Silver-Catalyzed CO2 Incorporation; Silver-Catalyzed Carbene, Nitrene, and Silylene Transfer Reactions; Asymmetric Silver-Catalyzed Reactions; Silver-Catalyzed Reduction and Oxidation of Aldehydes and Their Derivatives; Silver Complexes in Organic Transformations; and Silver Nanoparticles in Organic Transformations. -Covers recently developed organic reactions catalyzed by silver, along with their reaction mechanism -Introduces many new reactions and mechanisms related to silver catalysis -Offers professionals and newcomers in the related fields a survey of new advances in silver catalysis in organic synthesis Silver Catalysis in Organic Synthesis will appeal to a wide readership including chemists, biochemists, pharmaceutical scientists, biomedical researchers, agriculture scientists, and graduate students in the related fields.
Book Synopsis The Organic Coloring Book by : Neil Garg
Download or read book The Organic Coloring Book written by Neil Garg and published by . This book was released on 2017-04-22 with total page 30 pages. Available in PDF, EPUB and Kindle. Book excerpt: This coloring book brings to life the magic and impact of organic chemistry for children and adults alike. With more than 25 pages to color, kids will have fun and even learn some science too! The molecules featured in this book include sucrose, aspirin, caffeine, cellulose, proteins, and many more. This educational coloring book was created by two children, with the help of their father, a UCLA Chemistry Professor. "This coloring book brings the unbridled curiosity of a young mind together with the wonders of our molecular world in ways that will surely inspire discovery, fun, and perhaps a lifelong appreciation of the ubiquity and impact of chemistry" -Professor Paul Wender (Stanford University)
Book Synopsis Molecular Rearrangements in Organic Synthesis by : Christian M. Rojas
Download or read book Molecular Rearrangements in Organic Synthesis written by Christian M. Rojas and published by John Wiley & Sons. This book was released on 2015-10-26 with total page 774 pages. Available in PDF, EPUB and Kindle. Book excerpt: Designed for practitioners of organic synthesis, this book helps chemists understand and take advantage of rearrangement reactions to enhance the synthesis of useful chemical compounds. Provides ready access to the genesis, mechanisms, and synthetic utility of rearrangement reactions Emphasizes strategic synthetic planning and implementation Covers 20 different rearrangement reactions Includes applications for synthesizing compounds useful as natural products, medicinal compounds, functional materials, and physical organic chemistry
Book Synopsis Heterocycles in Natural Product Synthesis by : Krishna C. Majumdar
Download or read book Heterocycles in Natural Product Synthesis written by Krishna C. Majumdar and published by John Wiley & Sons. This book was released on 2011-06-15 with total page 648 pages. Available in PDF, EPUB and Kindle. Book excerpt: Filling a gap on the market, this handbook and ready reference is unique in its discussion of the usefulness of various heterocyclic systems in the synthesis of natural products. Clearly structured for easy access to the information, each chapter is devoted to a certain class of heterocycle, providing a tabular presentation of the natural products to be covered containing the particular heterocyclic ring system along with their biological profile, occurrence and most important physical properties, backed by the appropriate references. In addition, the application of the heterocyclic system to the synthesis of natural products ic covered in detail. Of great interest to organic, natural products, medicinal and biochemists, as well as those working in the pharmaceutical and agrochemical industry.
Author :Hans-Joachim Knoelker Publisher :Springer Science & Business Media ISBN 13 :3642255280 Total Pages :268 pages Book Rating :4.6/5 (422 download)
Book Synopsis Alkaloid Synthesis by : Hans-Joachim Knoelker
Download or read book Alkaloid Synthesis written by Hans-Joachim Knoelker and published by Springer Science & Business Media. This book was released on 2012-01-13 with total page 268 pages. Available in PDF, EPUB and Kindle. Book excerpt: Lycopodium Alkaloids: Isolation and Asymmetric Synthesis, by Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, by Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, by Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, by Yasuyuki Kita and Hiromichi Fujioka.- Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids, by Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, by Ingmar Bauer and Hans-Joachim Knölker.-
Book Synopsis Greene's Protective Groups in Organic Synthesis by : Peter G. M. Wuts
Download or read book Greene's Protective Groups in Organic Synthesis written by Peter G. M. Wuts and published by John Wiley & Sons. This book was released on 2012-12-20 with total page 1108 pages. Available in PDF, EPUB and Kindle. Book excerpt: The Fourth Edition of Greene's Protective Groups in Organic Synthesis continues to be an indispensable reference for controlling the reactivity of the most common functional groups during a synthetic sequence. This new edition incorporates the significant developments in the field since publication of the third edition in 1998, including... New protective groups such as the fluorous family and the uniquely removable 2-methoxybenzenesulfonyl group for the protection of amines New techniques for the formation and cleavage of existing protective groups, with examples to illustrate each new technique Expanded coverage of the unexpected side reactions that occur with protective groups New chart covering the selective deprotection of silyl ethers 3,100 new references from the professional literature The content is organized around the functional group to be protected, and ranges from the simplest to the most complex and highly specialized protective groups.
Book Synopsis Handbook of Asymmetric Heterogeneous Catalysis by : Kuiling Ding
Download or read book Handbook of Asymmetric Heterogeneous Catalysis written by Kuiling Ding and published by John Wiley & Sons. This book was released on 2008-10-20 with total page 467 pages. Available in PDF, EPUB and Kindle. Book excerpt: In this most up-to-date handbook each chapter contains a general introduction, followed by the principles of the immobilization and, finally, applications. In this way, it covers the most important approaches currently employed for the heterogenization of chiral catalysts, including data tables, applications, reaction types and literature citations. For chemists in both academia and industry as well as those working in the fine chemical and pharmaceutical industry.
