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Stereoselective Syntheses Of Certain Natural Products And Their Analogues From Chiral Pool And Enzymatically Derived Building Blocks
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Book Synopsis Stereoselective Syntheses of Certain Natural Products and Their Analogues from Chiral-pool and Enzymatically-derived Building Blocks by : Joshua Neil Victor Timshell Buckler
Download or read book Stereoselective Syntheses of Certain Natural Products and Their Analogues from Chiral-pool and Enzymatically-derived Building Blocks written by Joshua Neil Victor Timshell Buckler and published by . This book was released on 2018 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: This thesis is comprised of six scientific articles and is preceded by an overview that contextualises all of this published/submitted work. The first section of this thesis is comprised of Publications 1-3 and is concerned with the synthesis of novel, oxygenated analogues of the natural and non-natural enantiomeric forms of the Amaryllidaceae alkaloid galanthamine, a reversible and selective acetylcholine esterase (AChE) inhibitor that is used clinically in the treatment of Alzheimer's disease. Specifically, Publication 1 is an invited book chapter that details synthetic approaches to galanthamine and certain analogues pursued by the Banwell Group. It contextualises the strategy employed in preparing oxygenated analogues of galanthamine by the author in latter part of the first section of this thesis. Publication 2 is an invited review article that showcases the methodologies that have been developed within the Banwell Group for manipulating enzymatically-derived and homochiral cis-1,2-dihydrocatechols so as to generate a significant range of biologically active natural products. Publication 3 describes the synthesis of certain oxygenated derivatives of both (+)- and (-)-galanthamine and the evaluation of these as AChE inhibitors. The second section of this thesis is comprised of Publications 4 and 5. These detail the synthesis of certain polyfunctionalized, cyclohexene-based chirons from L-(+)- and D-(-)-tartaric acid, respectively, and their elaboration into various natural product scaffolds. Specifically, Publication 4 describes the preparation of the aforementioned chirons from L-(+)-tartaric acid and its elaboration to the enantiomer of a key intermediate described in Publication 3 that is used to produce oxygenated analogues of (-)-galanthamine. Publication 5 further demonstrates the utility of these new chirons in total synthesis by employing the enantiomer of this chiron (prepared from D-(+)-tartaric acid) as a key intermediate in the first total synthesis of the structurally unusual natural product aspergillusol B. The final section of this thesis is comprised of Publication 6. This details work on the total synthesis of the four diastereomeric forms of the pro-angiogenic guaiacylglycerol 8-O-4ʹ-coniferyl ethers (GGCE) in an effort to establish the role stereochemistry plays on their capacities to act as pro-angiogenic agents. The syntheses feature an Evans/Seebach syn-aldol reaction utilising auxiliaries derived from either L-(+)- or D-(-)-valine. In the case of syntheses of the anti-compounds this was followed by a Mitsunobu inversion of the benzylic alcohol. The four diastereomers were assessed for their pro-angiogenic properties in a human microvascular endothelial cell tubule assay. Whilst they were all active, the compounds containing the 8S-ether linkage were the most potent.
Book Synopsis Stereoselective Synthesis of Drugs and Natural Products by : Vasyl Andrushko
Download or read book Stereoselective Synthesis of Drugs and Natural Products written by Vasyl Andrushko and published by John Wiley & Sons. This book was released on 2013-08-16 with total page 1836 pages. Available in PDF, EPUB and Kindle. Book excerpt: Brings together the best tested and proven stereoselective synthetic methods Both the chemical and pharmaceutical industries are increasingly dependent on stereoselective synthetic methods and strategies for the generation of new chiral drugs and natural products that offer specific 3-D structures. With the publication of Stereoselective Synthesis of Drugs and Natural Products, researchers can turn to this comprehensive two-volume work to guide them through all the core methods for the synthesis of chiral drugs and natural products. Stereoselective Synthesis of Drugs and Natural Products features contributions from an international team of synthetic chemists and pharmaceutical and natural product researchers. These authors have reviewed the tremendous body of literature in the field in order to compile a set of reliable, tested, and proven methods alongside step-by-step guidance. This practical resource not only explores synthetic methodology, but also reaction mechanisms and applications in medicinal chemistry and drug discovery. The publication begins with an introductory chapter covering general principles and methodologies, nomenclature, and strategies of stereoselective synthesis. Next, it is divided into three parts: Part One: General Methods and Strategies Part Two: Stereoselective Synthesis by Bond Formation including C-C bond formation C-H bond formation C-O bond formation C-N bond formation Other C-heteroatom formation and other bond formation Part Three: Methods of Analysis and Chiral Separation References in every chapter serve as a gateway to the literature in the field. With this publication as their guide, chemists involved in the stereoselective synthesis of drugs and natural products now have a single, expertly edited source for all the methods they need.
Book Synopsis Chiral Building Blocks in Asymmetric Synthesis by : Jacek Wojaczynski
Download or read book Chiral Building Blocks in Asymmetric Synthesis written by Jacek Wojaczynski and published by John Wiley & Sons. This book was released on 2022-08-05 with total page 692 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chiral Building Blocks in Asymmetric Synthesis A comprehensive introduction to the important classes of chiral building blocks Chirality — the asymmetric quality found in certain chemical compounds — plays an essential role in our world: chiral compounds can be found in biology, pharmaceutical compounds, agrochemicals, and fragrances. The stereoselective preparation of these complex molecular constructions constitutes a challenge. To this end, modern asymmetric synthesis utilizes a variety of valuable and efficient reagents employed as chiral auxiliaries, metal complexes and organocatalysts in stereoselective catalysis, and enantiopure reactants termed as chiral building blocks. In Chiral Building Blocks in Asymmetric Synthesis, the achievements in the fields of preparation of and applications of chiral blocks are presented. In doing so, the book comprehensively discusses the important classes of these reactants as the key for the asymmetric synthesis of chiral molecules. As such, it is an indispensable resource about synthetic methods, as well as possible modifications and transformations of important classes of chiral compounds. It also highlights the importance of their use as reactants and auxiliaries in the preparation of more sophisticated molecules or supramolecular systems. In Chiral Building Blocks in Asymmetric Synthesis readers will also find: Organization according to the most important compound classes — e.g. amino acids, BINOL and its derivatives, terpenes, and others — with an emphasis on synthesis and application A focus on the use of chiral building blocks for the preparation of bioactive compounds and supramolecular assemblies Chiral Building Blocks in Asymmetric Synthesis is a useful reference for organic chemists, catalytic chemists, chemists in industry, medicinal chemists, pharmaceutical chemists, and the libraries that support them.
Book Synopsis Enzyme-Mediated Stereoselective Synthesis by : Stefano Serra
Download or read book Enzyme-Mediated Stereoselective Synthesis written by Stefano Serra and published by MDPI. This book was released on 2019-12-06 with total page 116 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book is a collection of studies focused on the exploitation of enzyme stereoselectivity for the synthesis of relevant chemicals, such as innovative materials, chiral building blocks, natural products, and flavor and fragrance compounds. Different catalytic approaches are reported. The first study describes a resolution-based process for the stereoselective synthesis of the enantiomeric forms of the flavor compound linaloyl oxide, whereas other enantiomeric enriched aroma compounds were obtained through a novel microbial approach based on solid-state fermentation. Two relevant works exploit the potential of the biocatalyzed reduction reactions. The first of these contributions describes the enantioselective synthesis of β-nitroalcohols by enzyme-mediated reduction of α-nitroketones, whereas a second contribution reports the preparation of chiral 1,4-diaryl-1,4-diols through ADH-catalyzed bioreduction of the corresponding diketones. Concerning enantioenriched alcohol derivatives, natural hydroxy fatty acids are prepared by means of the biocatalytic hydration reaction of natural fatty acids using the probiotic bacterium Lactobacillus rhamnosus as a whole-cell biocatalyst. Further studies describe the use of modified pullulan polysaccharide for lipase immobilization and the recent advances in synthetic applications of ω-transaminases for the production of chiral amines.
Book Synopsis Studies in Natural Products Chemistry by : Atta-ur Rahman
Download or read book Studies in Natural Products Chemistry written by Atta-ur Rahman and published by Elsevier. This book was released on 1995-08-10 with total page 772 pages. Available in PDF, EPUB and Kindle. Book excerpt: Studies in Natural Products Chemistry
Book Synopsis Studies in Natural Products Chemistry by : Atta-ur-Rahman
Download or read book Studies in Natural Products Chemistry written by Atta-ur-Rahman and published by Elsevier. This book was released on 2013-10-22 with total page 939 pages. Available in PDF, EPUB and Kindle. Book excerpt: Studies in Natural Products Chemistry, Volume 14: Stereoselective Synthesis, Part I is a collection of discourses on the stereoselective synthesis of the anticancer anthrucycline antibiotics; tetramic acid antibiotics; 3-and 4-deoxyhexoses; polysaccharides; levoglucosenone as precursor to natural products; synthesis of oligoribonucleotides; and oxidation of guaiazulene. This volume deals with a broad range of natural products focusing on the synthesis of antibiotics and anticancer agents — anthracyclines, tetramic acid, taxodione, vinblastine, and vincristine. These aforementioned drugs are used for the treatment of cancer (anthracyclines) and Hodgkin's disease and childhood acute leukemia (vinblastine and vincristine). The importance of the latest developments in the stereocontrolled synthesis of polysaccharides is discussed as polysaccharides play a fundamental role in cell life and have many technical applications. The synthesis of bioactive carbohydrates 3- and 4-deoxy-hexoses is compared with the more occurring deoxyhexoses in nature such as the 2-deoxy, 6-deoxy, and 2,6-dideoxy-hexoses, because the former are rare compounds and useful tools in the study of biological and biochemical properties of mono- and oligosaccharides, glycoproteins, and antibiotics. Alkaloids derived from Apocynaceae are known for their medicinal properties; hence the synthetic approaches to vinblastine and vincristine are discussed. Because of the minute amounts available from herbal sources, efforts toward their chemical synthesis are given more reference. This book can be a useful reference for the organic chemists. Chemical researchers, pharmaceutical scientists, and professionals of bioorganic chemistry will likewise gain a lot from this collection.
Book Synopsis Studies in Natural Products Chemistry by : Atta-ur Rahman
Download or read book Studies in Natural Products Chemistry written by Atta-ur Rahman and published by Elsevier. This book was released on 1996-05-01 with total page 1109 pages. Available in PDF, EPUB and Kindle. Book excerpt: In Volume 18 of this well-established series, Professor Atta-ur-Rahman again brings together the work of several of the world's leading authorities in organic chemistry. Their contributions demonstrate the rapid, ongoing development of this field by illustrating many of the latest advances in synthetic methods, total synthesis, structure determination, biosynthetic pathways, and biological activity.The opening chapter presents an overview of strategies for the synthesis of several classes of natural products with an emphasis on complex polycyclic systems. Subsequent chapters discuss the synthesis of specific classes of compounds, including morphine, polyketides, acetogenins, nonactic acid derivatives, complex spirocyclic ethers, ä-lactam and pyridone derivatives, inositol phosphates, sphingolipids, brassinosteroids, Hernandia lignans, and dimeric steroidal pyrazine alkaloids. Finally, the ever stronger links between chemistry and biology are reinforced by chapters on the origin and function of secondary metabolites, bioactive conformations of gastrin hormones, and immunochemistry.
Book Synopsis Classics in Stereoselective Synthesis by : Erick M. Carreira
Download or read book Classics in Stereoselective Synthesis written by Erick M. Carreira and published by John Wiley & Sons. This book was released on 2009-02-09 with total page 664 pages. Available in PDF, EPUB and Kindle. Book excerpt: Die wichtigsten und nützlichsten Methoden der modernen stereoselektiven Synthese sind in diesem Band zusammengefasst. Viele anschauliche Beispiele für die Darstellung von Wirkstoffen und Naturstoffen regen zur gezielten Abwandlung und Integration in eigene Synthesewege an. Dabei geht es den Autoren weniger darum, das Gebiet in seiner Gesamtheit darzustellen; vielmehr versuchen sie, die wirklich grundlegenden Ansätze auszuwählen, die jeder organische Synthesechemiker kennen und anwenden sollte.
Book Synopsis Enzyme-Mediated Stereoselective Synthesis by : Stefano Serra
Download or read book Enzyme-Mediated Stereoselective Synthesis written by Stefano Serra and published by . This book was released on 2019 with total page 116 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book is a collection of studies focused on the exploitation of enzyme stereoselectivity for the synthesis of relevant chemicals, such as innovative materials, chiral building blocks, natural products, and flavor and fragrance compounds. Different catalytic approaches are reported. The first study describes a resolution-based process for the stereoselective synthesis of the enantiomeric forms of the flavor compound linaloyl oxide, whereas other enantiomeric enriched aroma compounds were obtained through a novel microbial approach based on solid-state fermentation. Two relevant works exploit the potential of the biocatalyzed reduction reactions. The first of these contributions describes the enantioselective synthesis of ?-nitroalcohols by enzyme-mediated reduction of ?-nitroketones, whereas a second contribution reports the preparation of chiral 1,4-diaryl-1,4-diols through ADH-catalyzed bioreduction of the corresponding diketones. Concerning enantioenriched alcohol derivatives, natural hydroxy fatty acids are prepared by means of the biocatalytic hydration reaction of natural fatty acids using the probiotic bacterium Lactobacillus rhamnosus as a whole-cell biocatalyst. Further studies describe the use of modified pullulan polysaccharide for lipase immobilization and the recent advances in synthetic applications of ?-transaminases for the production of chiral amines.
Book Synopsis Stereoselective Synthesis by : Eckhard Ottow
Download or read book Stereoselective Synthesis written by Eckhard Ottow and published by Springer Science & Business Media. This book was released on 2012-12-06 with total page 147 pages. Available in PDF, EPUB and Kindle. Book excerpt: Devising methods and reagents for stereoselective synthesis is an intellectually demanding venture. Six experts on diastereo- and enantioselective synthesis contributed their papers to this volume. They were presented at a symposium on stereoselective synthesis to honour Professor Dr. Dr. h.c. Rudolf Wiechert's achievements in medicinal chemistry research. The symposium was organized by the Schering AG on the occasion of Professor Wiechert's 65th birthday.
Book Synopsis Studies in Natural Products Chemistry by : Atta-ur Rahman
Download or read book Studies in Natural Products Chemistry written by Atta-ur Rahman and published by Elsevier. This book was released on 2013-10-22 with total page 541 pages. Available in PDF, EPUB and Kindle. Book excerpt: Studies in Natural Products Chemistry Volume 12: Stereoselective Synthesis (Part H) reviews the stereoselective synthetic and mechanistic chemistry of bicyclomycin. It discusses chemical studies of the taxane diterpenes; the synthetic methodology for 2-amino alcohols of biological interest; and the synthesis and structure of hydroxylated indolizidines. Some of the topics covered in the book are the synthetic routes to the oxahydrindene subunit of the avermectin-milbemycin family of antiparasitic agents; isolation, structure elucidation, biosynthesis, and biological activity of the avermectins; two-stage coupling process of macrolide antibiotics synthesis; and synthesis of the rifamycin S ansa-chain compound. The complete synthesis of erythromycin A is also covered. The role of isocyanides in the synthesis of beta lactam antibiotics and the characteristics of the beta lactam antibiotics are discussed. The development of an A-Ring annulation strategy for taxane synthesis is also presented. A chapter is devoted to the advances in the synthesis of tumor-promoting diterpenes. The book can provide useful information to chemists, biologists, students, and researchers.
Book Synopsis Stereoselective Synthesis by : Eckhard Ottow
Download or read book Stereoselective Synthesis written by Eckhard Ottow and published by . This book was released on 1993-12-16 with total page 156 pages. Available in PDF, EPUB and Kindle. Book excerpt: A symposium on stereoeselective synthesis was organized by the Schering AG to honour Professor Dr. Dr. h.c. Rudolf Wiechert's 65th birthday and his achievements in over 30 years of successful medicinal chemistry research. The six plenary lectures by leading scientists are published in this book. The contributions highlight recent progress on diastereo- and enantioselective synthesis. Intriguing methodological work, synthesis of homochiral building blocks and elegant and highly efficient applications to the synthesis of stereochemically demanding targetmolecules are presented. From the Contents: Steroids and Stereochemistry- Enantioselective Catalysis with Chiral Metal Complexes - New Aspects in Stereoselective Synthesis of Aminoalcohols and Amino Acids - Enzymemimetic C-C and C-N Bond Formations - Synthesis of Natural Product of Polyketide Origin, An Exemplary Case - Progress in the Diels/Alder Reaction Means Progress in Steroid Synthesis
Book Synopsis Stereoselective Synthesis of Drugs and Natural Products, 2 Volume Set by : Vasyl Andrushko
Download or read book Stereoselective Synthesis of Drugs and Natural Products, 2 Volume Set written by Vasyl Andrushko and published by Wiley. This book was released on 2013-10-07 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Brings together the best tested and proven stereoselective synthetic methods Both the chemical and pharmaceutical industries are increasingly dependent on stereoselective synthetic methods and strategies for the generation of new chiral drugs and natural products that offer specific 3-D structures. With the publication of Stereoselective Synthesis of Drugs and Natural Products, researchers can turn to this comprehensive two-volume work to guide them through all the core methods for the synthesis of chiral drugs and natural products. Stereoselective Synthesis of Drugs and Natural Products features contributions from an international team of synthetic chemists and pharmaceutical and natural product researchers. These authors have reviewed the tremendous body of literature in the field in order to compile a set of reliable, tested, and proven methods alongside step-by-step guidance. This practical resource not only explores synthetic methodology, but also reaction mechanisms and applications in medicinal chemistry and drug discovery. The publication begins with an introductory chapter covering general principles and methodologies, nomenclature, and strategies of stereoselective synthesis. Next, it is divided into three parts: Part One: General Methods and Strategies Part Two: Stereoselective Synthesis by Bond Formation including C-C bond formation C-H bond formation C-O bond formation C-N bond formation Other C-heteroatom formation and other bond formation Part Three: Methods of Analysis and Chiral Separation References in every chapter serve as a gateway to the literature in the field. With this publication as their guide, chemists involved in the stereoselective synthesis of drugs and natural products now have a single, expertly edited source for all the methods they need.
Book Synopsis Principles of Asymmetric Synthesis by : R.E. Gawley
Download or read book Principles of Asymmetric Synthesis written by R.E. Gawley and published by Elsevier. This book was released on 1996-11-21 with total page 395 pages. Available in PDF, EPUB and Kindle. Book excerpt: The world is chiral. Most of the molecules in it are chiral, and asymmetric synthesis is an important means by which enantiopure chiral molecules may be obtained for study and sale. Using examples from the literature of asymmetric synthesis (more than 1300 references), the aim of this book is to present a detailed analysis of the factors that govern stereoselectivity in organic reactions. It is important to note that the references were each individually checked by the authors to verify relevance to the topics under discussion. The study of stereoselectivity has evolved from issues of diastereoselectivity, through auxiliary-based methods for the synthesis of enantiomerically pure compounds (diastereoselectivity followed by separation and auxiliary cleavage), to asymmetric catalysis. In the latter instance, enantiomers (not diastereomers) are the products, and highly selective reactions and modern purification techniques allow preparation - in a single step - of chiral substances in 99% ee for many reaction types. After an explanation of the basic physical-organic principles of stereoselectivity, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Analytical Methods" provides a critical overview of the most common methods for analysis of stereoisomers. The authors then follow the 'tried-and-true' format of grouping the material by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions (enolate alkylations, organometal additions to carbonyls, aldol and Michael reactions, and cycloadditions and rearrangements), one chapter on reductions and hydroborations (carbon-hydrogen bond forming reactions), and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). Leading references are provided to natural product synthesis that have been accomplished using a given reaction as a key step. In addition to tables of examples that show high selectivity, a transition state analysis is presented to explain - to the current level of understanding - the stereoselectivity of each reaction. In one case (Cram's rule) the evolution of the current theory is detailed from its first tentative (1952) postulate to the current Felkin-Anh-Heathcock formalism. For other reactions, only the currently accepted rationale is presented. Examination of these rationales also exposes the weaknesses of current theories, in that they cannot always explain the experimental observations. These shortcomings provide a challenge for future mechanistic investigations.
Download or read book Stereoselective Synthesis written by and published by . This book was released on 1989 with total page 756 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Stereoselective Syntheses of Tetrahydropyrans by : Kiyoun Lee
Download or read book Stereoselective Syntheses of Tetrahydropyrans written by Kiyoun Lee and published by Springer. This book was released on 2014-07-08 with total page 198 pages. Available in PDF, EPUB and Kindle. Book excerpt: In his thesis, Kiyoun Lee describes his studies into tandem and organocatalytic oxa-conjugate addition reactions for the synthesis of complex tetrahydropyrans (THP). Readers gain insight into the new methods Lee employs for the synthesis of biologically interesting natural products including (+)-leucascandrolide A, (+)-dactylolide, and (±)diospongin A. The reactions Lee investigates are applicable to a broad range of substrates and proceed with excellent stereoselectivity. Moreover, the methodologies allow the synthesis of a wide range of THP-containing compounds. The development of reactions, such as those discussed by Lee, has the potential to impact natural product synthesis, pharmaceutical development and chemical biology.
Book Synopsis The Total Synthesis of Natural Products, Volume 1 by : John ApSimon
Download or read book The Total Synthesis of Natural Products, Volume 1 written by John ApSimon and published by John Wiley & Sons. This book was released on 2009-09-22 with total page 618 pages. Available in PDF, EPUB and Kindle. Book excerpt: Each volume reviews the total synthesis of a set of compounds looking at syntheses reported historically and at the practice current at the time of publication. From volume 1 focusing on carbohydrates, prostagladins, nucleic acids, antibiotics, naturally occurring oxygen ring compounds and pyrrole pigments, the series continues with coverage of aromatic steroids, monoterpenes, triterpenes, sesquiterpenes, cannabinoids, natural inophores, insect pheromones and alkaloids. Volumes revisit the total synthesis of key compounds such as carbohydrates, nucleic acids and pyrrole pigments several times during the series building a picture of the historic development of total synthesis techniques for these major groups. Chapters are edited by experts in their field to give a complete overview of the best in the field at the time.
