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Strategies Towards The Synthesis Of Welwitindolinone C
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Book Synopsis Strategies Towards the Synthesis of Welwitindolinone C by : Jennifer Pitzen
Download or read book Strategies Towards the Synthesis of Welwitindolinone C written by Jennifer Pitzen and published by . This book was released on 2015 with total page 207 pages. Available in PDF, EPUB and Kindle. Book excerpt: Progress towards the total synthesis of N-methylwelwitindolinone C isothiocyanate is reported. The tetracyclic core is established by a key alkylation--type 2 intramolecular Diels--Alder cascade reaction, forming three new carbon-carbon bonds and five stereocenters in one step. Mechanistic studies suggest that alkylation proceeds via a zinc enolate intermediate instead of a silyl ketene aminal, shortening the synthesis by one step. Elaboration of the welwitindolinone core was accomplished with novel use of chlorinating agent MoCl5 to selectively convert a ketone to the vinyl chloride found in the natural product. To circumvent the problematic differentiation of two esters and install a bridgehead amine at an early stage in the synthesis, a series of new dienophiles were prepared. Ultimately selective protection of a diol intermediate allowed for differentiation, but methylation to install the final quaternary center proved to be challenging and remains one of the last hurdles in completing the synthesis.
Book Synopsis Total Synthesis of Welwitindolinone Natural Products by : Alexander David Huters
Download or read book Total Synthesis of Welwitindolinone Natural Products written by Alexander David Huters and published by . This book was released on 2013 with total page 254 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter one provides a summary of efforts towards the syntheses of the welwitindolinones with bicyclo[4.3.1]decane cores. Emphasis is given to more recent approaches that have successfully assembled the bicyclic core of the natural products. Chapters two and three are a discussion of our studies relating to a model system of the welwitindolinone natural products. Chapter two focuses on the use of an aryne cyclization to assemble the bicyclo[4.3.1]decane framework of the welwitindolinones. Chapter three covers initial attempts to install the bridgehead nitrogen substituent present in the natural products in addition to the synthesis of a functionalized aryne cyclization substrate. Chapters four and five present our total syntheses of the welwitindolinone natural products. The enantiospecific total syntheses of N-methylwelwitindolinone C isothiocyanate, N-methylwelwitindolinone C isonitrile, 3-hydroxy-N-methylwelwitindolinone C isothiocyanate and 3-hydroxy-N-methylwelwitindolinone C isonitrile are detailed. The 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 late-stage nitrene insertion reaction to install the bridgehead nitrogen substituent. The use of a deuterium kinetic isotope effect to improve the yield of the nitrene insertion is also presented. In addition, a computational method to predict the stereochemistry of a previously unconfirmed stereocenter in the hydroxylated natural products as well as experimental validation of the computational findings is discussed.
Book Synopsis More Dead Ends and Detours by : Miguel A. Sierra
Download or read book More Dead Ends and Detours written by Miguel A. Sierra and published by John Wiley & Sons. This book was released on 2013-07-11 with total page 297 pages. Available in PDF, EPUB and Kindle. Book excerpt: Success comes in many forms and in synthesis it can be a failure that results in their ultimate successful solutions. This long-awaited sequel to "Dead Ends and Detours" retains the proven concept while featuring over 20 new case studies of failed strategies and their (successful) solutions in natural product total synthesis. Additionally, computational models are used to discuss the problem in much more detail and to provide readers with additional information not found in the primary literature. The topics range from classic synthetic reactions (e.g. Diels Alder reaction), metal-mediated coupling reactions, metathesis, and asymmetric catalysis to the importance of protecting and activating groups. This book will benefit not only graduate students in organic chemistry but also advanced researchers as they gain knowledge derived from the step-by-step analysis of mistakes made in the past and, thus be able to improve their own chemical reaction planning. With its coverage of the most commonly applied reaction types, the book perfectly complements its predecessor, which focuses on general aspects, such as reactivity and selectivity.
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.
Book Synopsis Classics in Total Synthesis III by : K. C. Nicolaou
Download or read book Classics in Total Synthesis III written by K. C. Nicolaou and published by John Wiley & Sons. This book was released on 2011-03-14 with total page 788 pages. Available in PDF, EPUB and Kindle. Book excerpt: K.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry Adopting his didactically skillful approach, K.C. Nicolaou compiles in this textbook the important synthetic methods that lead to a complex molecule with valuable properties. He explains all the key steps of the synthetic pathway, highlighting the major developments in blue-boxed sections and contrasting these to other synthetic methods. A wonderful tool for learning and teaching and a must-have for all future and present organic and biochemists.
Book Synopsis The Development of a Method for Rhodium-catalyzed Olefin Aziridination and Its Application to Synthesis of the Welwitindolinones by : Kiran Guthikonda
Download or read book The Development of a Method for Rhodium-catalyzed Olefin Aziridination and Its Application to Synthesis of the Welwitindolinones written by Kiran Guthikonda and published by . This book was released on 2008 with total page 322 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book The Alkaloids written by and published by Elsevier. This book was released on 2013-12-19 with total page 358 pages. Available in PDF, EPUB and Kindle. Book excerpt: This series is world-renowned as the leading compilation of current reviews of this vast field. Internationally acclaimed for more than 40 years, The Alkaloids, founded by the late Professor R.H.F. Manske, continues to provide outstanding coverage of this rapidly expanding field. Each volume provides, through its distinguished authors, up-to-date and detailed coverage of particular classes or sources of alkaloids. - Up-to-date reviews on a large and very important group of natural products from both a chemical and biological perspective - Comprehensive, dynamic reviews written by leading authors in the respective fields - Broad coverage on the biological aspects
Book Synopsis Nickel-catalyzed Cross-coupling of Phenol Derivatives and Total Synthesis of Welwitindolinone Natural Products by : Kyle Wayne Quasdorf
Download or read book Nickel-catalyzed Cross-coupling of Phenol Derivatives and Total Synthesis of Welwitindolinone Natural Products written by Kyle Wayne Quasdorf and published by . This book was released on 2012 with total page 369 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter one provides a survey of the wide variety of unconventional phenol derivatives that are now available for use in traditional cross-coupling reactions. Emphasis is given to carbon-carbon (C-C) bond forming reactions with a brief discussion of other transformations. Chapters two and three are a discussion of our work in the field of nickel-catalyzed cross-coupling reactions of phenol derivatives. The use of aryl pivalates, sulfamates, carbamates, and carbonates in the nickel-catalyzed Suzuki-Miyaura coupling is described, along with synthetic applications utilizing these phenol derivatives. A computational and experimental mechanistic study for the cross-coupling of aryl sulfamates and carbamates is also reported. Chapters four and five detail our efforts in the total synthesis of the welwitindolinone natural products. The enantiospecific total syntheses of ( - )-N-methylwelwitindolinone C isothiocyanate and ( - )-N-methylwelwitindolinone C isonitrile, as well as their respective C3-hydroxylated analogs are reported. The synthetic routes feature an aryne cyclization to rapidly construct the [4.3.1]-bicyclic core of these molecules, as well as a late-stage intramolecular nitrene insertion to functionalize a bridgehead carbon. The strategic use of a deuterium kinetic isotope effect to improve the efficiency of the nitrene insertion is also discussed. A computational prediction for the stereochemical configuration at C3 of the hydroxylated welwitindolinones is presented, which was subsequently confirmed by experimental studies.
Book Synopsis Modern Heterocyclic Chemistry, 4 Volumes by : Julio Alvarez-Builla
Download or read book Modern Heterocyclic Chemistry, 4 Volumes written by Julio Alvarez-Builla and published by John Wiley & Sons. This book was released on 2011-08-15 with total page 2531 pages. Available in PDF, EPUB and Kindle. Book excerpt: Eine Fülle von Information zum attraktiven Preis bietet Ihnen dieses vierbändige Handbuch der Heterocyclenchemie.
Book Synopsis Efficiency in Natural Product Total Synthesis by : Pei-Qiang Huang
Download or read book Efficiency in Natural Product Total Synthesis written by Pei-Qiang Huang and published by John Wiley & Sons. This book was released on 2018-07-24 with total page 512 pages. Available in PDF, EPUB and Kindle. Book excerpt: Uniting the key organic topics of total synthesis and efficient synthetic methodologies, this book clearly overviews synthetic strategies and tactics applied in total synthesis, demonstrating how the total synthesis of natural products enables scientific and drug discovery. • Focuses on efficiency, a fundamental and important issue in natural products synthesis that makes natural product synthesis a powerful tool in biological and pharmaceutical science • Describes new methods like organocatalysis, multicomponent and cascade reactions, and biomimetic synthesis • Appeals to graduate students with two sections at the end of each chapter illustrating key reactions, strategies, tactics, and concepts; and good but unfinished total synthesis (synthesis of core structure) before the last section • Compiles examples of solid phase synthesis and continuing flow chemistry-based total synthesis which are very relevant and attractive to industry R&D professionals
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 Rhodium Catalysis by : Carmen Claver
Download or read book Rhodium Catalysis written by Carmen Claver and published by Springer. This book was released on 2017-12-15 with total page 291 pages. Available in PDF, EPUB and Kindle. Book excerpt: The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics of pure and applied organometallic chemistry, where new breakthroughs are being achieved that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Review articles are generally invited by the volume editors. All chapters from Topics in Organometallic Chemistry are published OnlineFirst with an individual DOI. In references, Topics in Organometallic Chemistry is abbrev iated as Top Organomet Chem and cited as a journal.
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 Progress Towards the Synthesis of N-methylwelwitindolinone C Isothiocyanate by : Sheng-Tung Huang
Download or read book Progress Towards the Synthesis of N-methylwelwitindolinone C Isothiocyanate written by Sheng-Tung Huang and published by . This book was released on 1999 with total page 96 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Biomimetic Organic Synthesis by : Erwan Poupon
Download or read book Biomimetic Organic Synthesis written by Erwan Poupon and published by John Wiley & Sons. This book was released on 2011-05-09 with total page 1024 pages. Available in PDF, EPUB and Kindle. Book excerpt: In this exciting 2 volume set, the approach and methodology of bio-inspired synthesis of complex natural products is laid out, backed by abundant practical examples from the authors' own work as well as from the published literature. Volume 1 describes the biomimetic synthesis of alkaloids. Volume 2 covers terpenes, polyketides, and polyphenols. A discussion of the current challenges and frontiers in biomimetic synthesis concludes this comprehensive handbook. Key features: Biomimetic Strategies have become an every-day tool not only for chemists but also for biologists. The synthetic applications are overwhelming, making this comprehensive 2 volume work a must-have for everyone working in the field. Unifying both synthetic and biosynthetic aspects, this book covers everything from organocatalysis and natural product synthesis to synthetic biology and even green chemistry.
Book Synopsis Advances in Heterocyclic Chemistry by : Alan R. Katritzky
Download or read book Advances in Heterocyclic Chemistry written by Alan R. Katritzky and published by Academic Press. This book was released on 2013-10-04 with total page 259 pages. Available in PDF, EPUB and Kindle. Book excerpt: Established in 1960, Advances in Heterocyclic Chemistry is the definitive serial in the area—one of great importance to organic chemists, polymer chemists and many biological scientists. Written by established authorities in the field, the comprehensive reviews combine descriptive chemistry and mechanistic insight and yield an understanding of how the chemistry drives the properties. - One of great importance to organic chemists, polymer chemists and many biological scientists - Written by established authorities in the field, the comprehensive reviews combine descriptive chemistry and mechanistic insight and yield an understanding of how the chemistry drives the properties
Book Synopsis Development of a Unified Strategy for the Asymmetric Synthesis of Lituarines A, B, and C. by : Shawn P. Walsh
Download or read book Development of a Unified Strategy for the Asymmetric Synthesis of Lituarines A, B, and C. written by Shawn P. Walsh and published by . This book was released on 2004 with total page 494 pages. Available in PDF, EPUB and Kindle. Book excerpt:
