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Author: Lucas Morrill Publisher: ISBN: Category : Languages : en Pages : 395
Book Description
This dissertation encompasses several projects pertaining to natural product total synthesis, reaction methodology development, and kinetic studies. The total synthesis of natural products continues to be a fruitful area of research in organic chemistry. The successful completion of a total synthesis endeavor not only affirms ambitious route designs, but can also allow access to significant amounts of biologically-active compounds. Given that natural product structures inspire the development of new agrochemicals and pharmaceuticals, their syntheses are a worthwhile endeavor. Also, the development of new reaction methodologies and the understanding of fundamental reactivities of many intermediates remain important areas of research. Chapter One offers a current perspective on the field of natural product total synthesis. Alhough historically viewed as a highly competitive field, several recent examples show the growing spirit of collaboration in total synthesis. By forming alliances with chemists in other fields, industries, or laboratories, total synthesis chemists have made many breakthroughs that would arguably not be possible if working independently. Chapters Two and Three describe our laboratory's total syntheses of several bioactive akuammiline alkaloids, including strictamine, 2(S)-cathafoline, akuammiline, -akuammigine, and 10-demethoxynorvincorine. Our strategic approach to the natural products focused on the use of a modern variant of a classic reaction, the Fischer indolization reaction, to install several rings and the common quaternary center found in each target. This strategy allowed for the first total syntheses of akuammilines bearing the methanoquinolizidine core and those that also bear vicinal quaternary centers. In addition, rearrangements of the methanoquinolizidine core were developed that allowed us to access pyrrolidinoindoline-containing akuammilines. Chapter Four describes a series of kinetic studies used to determine the electrophilicity parameter of benzyne and related aryne intermediates. Arynes are a family of strained intermediates whose existence has been postulated for over 100 years. Recent advances have confirmed their existence and proven their synthetic utility. An advanced knowledge of their reactivity thus far has remained elusive. Our laboratory employed the diffusion clock method to measure the rates of reaction between several arynes and a variety of different nucleophilic reaction partners. The result allowed for the first quantification of the electrophilicity of these strained intermediates and should influence synthetic planning in the future. Chapter Five includes a study in the development of reaction methodology. Utilizing a variant of the Fischer Indolization reaction, our laboratory discovered a general method for making aza-indoline structures. This methodology was applied in the synthesis of derivatives of akuammiline alkaloids and Alzheimer's therapeutic molecules. In addition, a predictive computational model of reactivity was derived.
Author: Lucas Morrill Publisher: ISBN: Category : Languages : en Pages : 395
Book Description
This dissertation encompasses several projects pertaining to natural product total synthesis, reaction methodology development, and kinetic studies. The total synthesis of natural products continues to be a fruitful area of research in organic chemistry. The successful completion of a total synthesis endeavor not only affirms ambitious route designs, but can also allow access to significant amounts of biologically-active compounds. Given that natural product structures inspire the development of new agrochemicals and pharmaceuticals, their syntheses are a worthwhile endeavor. Also, the development of new reaction methodologies and the understanding of fundamental reactivities of many intermediates remain important areas of research. Chapter One offers a current perspective on the field of natural product total synthesis. Alhough historically viewed as a highly competitive field, several recent examples show the growing spirit of collaboration in total synthesis. By forming alliances with chemists in other fields, industries, or laboratories, total synthesis chemists have made many breakthroughs that would arguably not be possible if working independently. Chapters Two and Three describe our laboratory's total syntheses of several bioactive akuammiline alkaloids, including strictamine, 2(S)-cathafoline, akuammiline, -akuammigine, and 10-demethoxynorvincorine. Our strategic approach to the natural products focused on the use of a modern variant of a classic reaction, the Fischer indolization reaction, to install several rings and the common quaternary center found in each target. This strategy allowed for the first total syntheses of akuammilines bearing the methanoquinolizidine core and those that also bear vicinal quaternary centers. In addition, rearrangements of the methanoquinolizidine core were developed that allowed us to access pyrrolidinoindoline-containing akuammilines. Chapter Four describes a series of kinetic studies used to determine the electrophilicity parameter of benzyne and related aryne intermediates. Arynes are a family of strained intermediates whose existence has been postulated for over 100 years. Recent advances have confirmed their existence and proven their synthetic utility. An advanced knowledge of their reactivity thus far has remained elusive. Our laboratory employed the diffusion clock method to measure the rates of reaction between several arynes and a variety of different nucleophilic reaction partners. The result allowed for the first quantification of the electrophilicity of these strained intermediates and should influence synthetic planning in the future. Chapter Five includes a study in the development of reaction methodology. Utilizing a variant of the Fischer Indolization reaction, our laboratory discovered a general method for making aza-indoline structures. This methodology was applied in the synthesis of derivatives of akuammiline alkaloids and Alzheimer's therapeutic molecules. In addition, a predictive computational model of reactivity was derived.
Author: Akkattu T. Biju Publisher: John Wiley & Sons ISBN: 3527346465 Category : Science Languages : en Pages : 530
Book Description
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.
Author: Dipakranjan Mal Publisher: Elsevier ISBN: 0128138017 Category : Science Languages : en Pages : 466
Book Description
Anionic Annulations in Organic Synthesis: A Versatile and Prolific Class of Ring-Forming Reactions is a comprehensive review of the main annulations for the construction of cyclic structures and their use in the total synthesis of functional molecules. The book explores in detail the Hauser, Robinson, Sammes, and Myers annulations, all of which are beneficial to constructing substrates with complex molecular structures suitable for pharmaceutical purposes. This volume begins with an in-depth introduction on the history and perspectives of annulations. It then covers different categories of annulation in each chapter, examining their application to drug synthesis for a range of different medicinal compounds. Anionic Annulations in Organic Synthesis delivers a thorough analysis of the topic and provides the tools necessary to master anionic organic chemistry. It is a valuable resource for chemists, researchers, and students seeking a complete and detailed understanding of anionic annulations. Serves as a useful tool to both academic and industrial researchers in the field Includes numerous examples of anionic annulations and how to apply them practically in research and industry Features anionic annulations that are particularly effective for the synthesis of polyoxygenated polycyclic compounds
Author: Richard Sundberg Publisher: Elsevier ISBN: 0323147860 Category : Science Languages : en Pages : 505
Book Description
Organic Chemistry, Volume 18: The Chemistry of Indoles discusses the chemistry of indole derivatives. This book explores the potent biological activity of several indole derivatives and explains the structure of indole alkaloids. Organized into 10 chapters, this monograph starts with an overview of the most important types of reactions of the indole ring on a mechanical basis. This text then proceeds to review the methods of synthesizing indoles and describes the oxidations and rearrangements of indole derivatives. Other chapters explore the special features of the synthesis and reactivity of hydroxyindoles, acylindoles, and aminoindoles. This book discusses as well the properties of carboxyl groups, which is substituted on the benzenoid ring of the indole nucleus that is typical of aromatic carboxylic acids. The final chapter deals with the certain classes of indoles that are found in nature. Chemists, researchers, and readers interested in the chemistry of indoles will find this book extremely useful.
Author: Neil Garg Publisher: ISBN: 9780692860540 Category : Languages : en Pages : 30
Book Description
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)
Author: Tsutomu Ishikawa Publisher: John Wiley & Sons ISBN: 9780470740866 Category : Science Languages : en Pages : 336
Book Description
Guanidines, amidines and phosphazenes have been attracting attention in organic synthesis due to their potential functionality resulting from their extremely strong basicity. They are also promising catalysts because of their potential for easy molecular modification, possible recyclability, and reduced or zero toxicity. Importantly, these molecules can be derived as natural products – valuable as scientists move towards “sustainable chemistry”, where reagents and catalysts are derived from biomaterial sources. Superbases for Organic Synthesis is an essential guide to these important molecules for preparative organic synthesis. Topics covered include the following aspects: an introduction to organosuperbases physicochemical properties of organic superbases amidines and guanidines in organic synthesis phosphazene: preparation, reaction and catalytic role polymer-supported organosuperbases application of organosuperbases to total synthesis related organocatalysts: proton sponges and urea derivatives amidines and guanidines in natural products and medicines Superbases for Organic Synthesis is a comprehensive, authoritative and up-to-date guide to these important reagents for organic chemists, drug discovery researchers and those interested in the chemistry of natural products.
Author: Vishnu Ji Ram Publisher: Elsevier ISBN: 0081011911 Category : Science Languages : en Pages : 500
Book Description
Heterocycles are ubiquitously present in nature and occupy a unique place in organic chemistry as they are part of the DNA and haemoglobin that make life possible. The Chemistry of Heterocycles covers an introduction to the topic, followed by a chapter on the nomenclature of all classes of isolated, fused and polycyclic heterocycles. The third chapter delineates the highly strained three membered N,O and S containing aromatic and non-aromatic heterocycles with one and more than one similar and dissimilar heteroatom. The four-membered heterocycles are abundantly present in various natural and synthetic products of pharmacological importance. This chapter describes the natural abundance, synthesis, chemical reactivity, structural features and their medicinal importance. This class of compounds are present as sub-structures in penicillin and cytotoxic Taxol. Lastly, a chapter on the natural abundance, synthesis, chemical reactivity and pharmacological importance of 5-membered heterocycles with N,O,S heteroatom is covered. The chemistry of heterocycles with mixed heteroatom such as, N-S, N-O, N-S etc. is also described. Gives in-depth, clear information about various systems of nomenclature along with widely acceptable IUPAC system for naming various classes of heterocycles Provides complete information about natural occurrences, synthesis, chemical reactivity, pharmacological importance of heterocycles and their application in material science Highly relevant for graduate students and researchers, providing updated information about various isolated and fused N,O and,S containing heterocycles
Author: John Whittall Publisher: John Wiley & Sons ISBN: 1119487021 Category : Science Languages : en Pages : 560
Book Description
Provides clear and comprehensive coverage of recently developed applied biocatalysis for synthetic organic chemists with an emphasis to promote green chemistry in pharmaceutical and process chemistry This book aims to make biocatalysis more accessible to both academic and industrial synthetic organic chemists. It focuses on current topics within the applied industrial biocatalysis field and includes short but detailed experimental methods on timely novel biocatalytic transformations using new enzymes or new methodologies using known enzymes. The book also features reactions that are “expanding and making the enzyme toolbox available to chemists”—providing readers with comprehensive methodology and detailed key sourcing information of a wide range of enzymes. Chapters in Applied Biocatalysis: The Chemist’s Enzyme Toolkit are organized by reaction type and feature a short introductory section describing the current state of the art for each example. Much of the book focuses on processes for which the enzymes are readily available so that organic chemists can synthesize appropriate quantities of chemicals with available materials in a standard chemical laboratory. Advanced methods are included to present examples of new enzymes that might encourage collaboration with suppliers or academic groups and that will educate chemists of rapidly expanding future possibilities. Focuses on current topics within the applied industrial biocatalysis field Offers experimental methods on novel biocatalytic transformations using new enzymes or new methodology using known enzymes Covers the hot topics of enzyme and chemoenzymatic cascades and biocatalysis in flow Edited by noted experts from both academia and industry with years of experience in the field of biocatalysis—particularly, the industrial applications of enzymes Written for synthetic organic chemists working in all industries but especially the pharmaceutical industry and for those in academia with an eye for biocatalysis, Applied Biocatalysis: The Chemist’s Enzyme Toolkit will also benefit academic groups in chemistry and related sciences that are using enzymes for synthetic purposes, as well as those working in the area of enzymology and molecular biology.
Author: Gordon W. Gribble Publisher: John Wiley & Sons ISBN: 0470512180 Category : Science Languages : en Pages : 704
Book Description
Of the myriad of heterocycles known to man, the indole ring stands foremost for its remarkably versatile chemistry, its enormous range of biological activities, and its ubiquity in the terrestrial and marine environments. The indole ring continues to be discovered in natural products and to be employed in man-made pharmaceuticals and other materials. Given the enormous resurgence in indole ring synthesis over the past decade — highlighted by the power of transition metal catalysis — this authoritative guide addresses the need for a comprehensive presentation of the myriad of methods for constructing the indole ring, from the ancient to the modern, and from the obscure to the well-known. Following presentation of the classic indole ring syntheses and many newer methods, coverage continues with indole ring syntheses via pyrroles, indolines, oxindoles, isatins, radical and photochemical reactions, aryne cycloadditions. This extensive volume concludes with the modern transition metal–catalyzed indole ring syntheses that utilize copper, palladium, rhodium, gold, ruthenium, platinum, and other metals to fashion the indole ring Indole Ring Synthesis is a comprehensive, authoritative and up-to-date guide to the synthesis of this important heterocycle for organic chemists, pharmaceutical researchers and those interested in the chemistry of natural products.
Author: Lucas Morrill
Author: Lucas Morrill
Author: Akkattu T. Biju
Author: Dipakranjan Mal
Author: Richard Sundberg
Author: Neil Garg
Author: Tsutomu Ishikawa
Author: Jiro Tsuji
Author: Vishnu Ji Ram
Author: John Whittall
Author: Gordon W. Gribble