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Total Synthesis Of N Methylwelwitindolinone D Isonitrile
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Book Synopsis Total Synthesis of N-methylwelwitindolinone D Isonitrile by : Vikram Bhat
Download or read book Total Synthesis of N-methylwelwitindolinone D Isonitrile written by Vikram Bhat and published by . This book was released on 2011 with total page 250 pages. Available in PDF, EPUB and Kindle. Book excerpt: Synthesis of the characteristic bridged-bicylic skeleton of the welwitindolinone alkaloids was achieved via manganese(III) promoted oxidative cyclization and palladium catalyzed enolate arylation reactions. Total synthesis of N-methylwelwitindolinone D isonitrile was accomplished. Synthesis of 20,21-dihydro N-methylwelwitindolinone B isothiocyanate was also completed. During the course of these synthetic efforts, several interesting and unexpected observations were made.
Book Synopsis Enantiospecific Total Synthesis of Welwitindolinone Alkaloids by : Evan Daniel Styduhar
Download or read book Enantiospecific Total Synthesis of Welwitindolinone Alkaloids written by Evan Daniel Styduhar and published by . This book was released on 2015 with total page 222 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, three, and four present our total syntheses of the welwitindolinone natural products. The enantiospecific total syntheses of N-methylwelwitindolinone C isothiocyanate, N-methylwelwitindolinone D isonitrile, and N-methylwelwitindolinone B isothiocyanate 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 C-H nitrene insertion reaction to install the bridgehead nitrogen substituent. In chapter three, a dual C-H functionalization event installs the challenging ether linkage and allows for completion of ( - )-N-methylwelwitindolinone D isonitrile. Chapter four details a regio- and diastereoselective chlorinative oxabicyclic opening to enable the first total synthesis of N-methylwelwitindolinone B isothiocyanate.
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 : 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 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 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 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 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 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.
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 Organic Synthesis by : Douglass F. Taber
Download or read book Organic Synthesis written by Douglass F. Taber and published by Oxford University Press. This book was released on 2013-02-21 with total page 263 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organic Synthesis: State of the Art 2009-2011 is a convenient, concise reference that offers a summary of current research in organic synthesis. The fourth volume in the esteemed State of the Art series, the book complies two years' worth if Douglas Taber's popular weekly column, "Organic Chemistry Highlights." The series is an invaluable resource, leading chemists quickly and easily to the most significant developments in the field. -- Book Jacket.
Book Synopsis Studies Toward the Total Synthesis of Welwitindolinone A Isonitrile by : Tehshik P. Yoon
Download or read book Studies Toward the Total Synthesis of Welwitindolinone A Isonitrile written by Tehshik P. Yoon and published by . This book was released on 1999 with total page 100 pages. Available in PDF, EPUB and Kindle. Book excerpt:
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 Silver Catalysis in Organic Synthesis, 2 Volume Set by : Chao-Jun Li
Download or read book Silver Catalysis in Organic Synthesis, 2 Volume Set written by Chao-Jun Li and published by John Wiley & Sons. This book was released on 2019-04-29 with total page 848 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.
Download or read book Deuterium written by Jaemoon Yang and published by Elsevier. This book was released on 2016-05-15 with total page 132 pages. Available in PDF, EPUB and Kindle. Book excerpt: Deuterium: Discovery and Applications in Organic Chemistry provides a well-illustrated overview of the discovery of 2H or heavy hydrogen, the stable hydrogen isotope with both a proton and a neutron in its nucleus. The work introduces the isotope, its discovery, physical properties, nomenclature, and common compounds, also exploring its application in organic chemistry through classic and recent examples from literature. Finally, the book devotes one chapter to Deuterium in medicinal chemistry and the biological effects of Deuterium Oxide, better known as D2O. - Provides unique coverage not found elsewhere that is presented in an accessible, dedicated short work - Contains practical information and examples on the use of Deuterium (D or 2H, Heavy Hydrogen) in organic synthesis - Presents a detailed description of Deuterium's discovery and applications in the pharmaceutical industry
Book Synopsis The Development of Free Radical-mediated Aryl Amination and Its Application Toward the Total Synthesis of Ambiguine G Nitrile by : Rajesh Viswanathan
Download or read book The Development of Free Radical-mediated Aryl Amination and Its Application Toward the Total Synthesis of Ambiguine G Nitrile written by Rajesh Viswanathan and published by . This book was released on 2005 with total page 424 pages. Available in PDF, EPUB and Kindle. Book excerpt:
