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Asymmetric Synthesis Of Natural Products

Author: Ari M. P. Koskinen
Publisher: John Wiley & Sons
ISBN: 1118347331
Size: 30.77 MB
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Asymmetric Synthesis of Natural Products, 2nd Edition introduces students to this rapidly growing field of organic chemistry. The initial chapters present the foundations of asymmetric synthesis, including the theory and applications of individual asymmetric reactions. This is followed by chapters on each of the major individual classes of natural products; their structures, biosynthesis and interrelationships as well as examples of asymmetric syntheses and the practical value of these compounds. Natural product classes covered include carbohydrates, amino acids, peptides, proteins, nucleosides, nucleotides, nucleic acids, polyketides, isoprenoids, shikamic acid derivatives and alkaloids. For this second edition the text has been thoroughly updated and expanded, and includes new discussions and examples covering atom and redox economies, practical aspects and environmental awareness. Organocatalysis has emerged completely in the last ten years, and has been fully integrated into this new edition.

Asymmetric Synthesis Of Drugs And Natural Products

Author: Ahindra Nag
Publisher: CRC Press
ISBN: 1315302292
Size: 80.31 MB
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This book focuses on different techniques of asymmetric synthesis of important compounds, such as drugs and natural products. It gives insightful information on recent asymmetric synthesis by Inorganic, Organic and Enzymatic combinations. It also emphasizes chiral compounds and design of new catalyst for synthesis of compounds.

Asymmetric Synthesis Of Bioactive Lactones And The Development Of A Catalytic Asymmetric Synthesis Of Aryl Ketones

Author: Robert Doran
Publisher: Springer
ISBN: 3319205447
Size: 49.13 MB
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This thesis addresses two fundamental areas in contemporary organic chemistry: synthesis of natural products and catalytic asymmetric synthesis. Firstly, a new methodology, developed by our research group, which allows the asymmetric synthesis of lactones, a structural unit ubiquitous in natural products, was utilised in the synthesis of a number of natural product analogues that showed significant biological activity. Secondly, the development of a catalytic asymmetric synthesis of a key structural motif present in a number of natural products and pharmaceuticals was accomplished. During the course of this work we discovered dual stereo control, which is significant because it allows the configuration of a new stereo centre to be controlled by a simple change of proton source.

The Asymmetric Synthesis Of 1 4 Benzodioxane Lignan Natural Products

Author: Lisa Ivy Pilkington
Size: 71.49 MB
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Lignans are a large class of natural products defined as the products of an oxidative dimerisation of two or more phenylpropanoid units. 1,4-Benzodioxane neolignans are a significant subtype of lignan natural products that showcase a range of biological activities. Previous syntheses of 1,4-benzodioxane lignans are predominantly racemic and do not easily allow for the main points of variation between related and analogous products. This thesis focuses on the development of a flexible asymmetric synthesis of 1,4-benzodioxane compounds and its subsequent application to natural product synthesis. Initially, a model study was undertaken to investigate the key steps required in this synthesis. Following the model study, the developed synthesis was then applied to the first asymmetric synthesis of the rodgersinine family, successfully yielding all rodgersinine natural products 21, 83, 84 and 87 and their enantiomers. Through chiroptical analysis, it was found that the original assignment of 83 and 87 was incorrect, and the ECD comparison of 1,4-benzodioxane natural products and model compounds is not reliable. Members of the eusiderin family, eusiderins A (19), B (243), C (194), G (37), L (260) and M (245) and analogues were synthesised in a highly divergent manner from chiral aldehyde 259. An ECD study also confirmed the absolute stereochemistry of 19 and 194 from different natural sources, and provided a reference for stereochemical assignment of future eusiderins. The adaptation of the synthesis to 2-hydroxymethyl-1,4-benzodioxane neolignans was shown with the successful synthesis of (-)-isoamericanin A (24) and (+)-isoamericanol A (20). Further application of this synthesis to complex trilignan magnolianin 278 was unsuccessful following the failure to synthesise ether 351 because of steric restrictions. The formal asymmetric synthesis of silybin B (358) and isosilandrin B (364); 1,4-benzodioxane flavonolignans well-regarded for their potent activities, was achieved, demonstrating the applicability of the developed synthesis to this notable group of compounds. Subsequent testing by Eli Lilly and a leading anti-HCV expert, of selected synthesised 1,4-benzodioxane compounds identified them to exhibit activities with applications in areas of cancer and neurological treatments, as well as hepaprotective properties that are currently undergoing further exploration.

Principles And Applications Of Asymmetric Synthesis

Author: Guo-Qiang Lin
Publisher: John Wiley & Sons
ISBN: 0471465240
Size: 79.49 MB
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Asymmetric synthesis remains a challenge to practicing scientistsas the need for enantiomerically pure or enriched compoundscontinues to increase. Over the last decade, a large amount ofliterature has been published in this field. Principles andApplications of Asymmetric Synthesis consolidates and evaluates themost useful methodologies into a one-volume resource for theconvenience of practicing scientists and students. Authored by internationally renowned scientists in the field, thisreliable reference covers more than 450 reactions and includesimportant stoichiometric as well as catalytic asymmetric reactions.The first chapter reviews the basic principles, commonnomenclature, and analytical methods, and the remainder of the bookis organized according to reaction type. The text examines suchtopics as: Carbon-carbon bond formations involving carbonyls, enamines,imines, and enolates Asymmetric C-O bond formations including epoxidation,dihydroxylation, and aminohydroxylation Asymmetric synthesis using the Diels-Alder reaction and othercyclizations Applications to the total synthesis of natural products Use of enzymes in asymmetric synthesis Practicing chemists in the pharmaceutical, fine chemical, andagricultural professions as well as graduate students will findthat Principles and Applications of Asymmetric Synthesis affordscomprehensive and current coverage.

Asymmetric Synthesis Ii

Author: Mathias Christmann
Publisher: John Wiley & Sons
ISBN: 3527672591
Size: 71.34 MB
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After the overwhelming success of 'Asymmetric Synthesis - The Essentials', narrating the colorful history of asymmetric synthesis, this is the second edition with latest subjects and authors. While the aim of the first edition was mainly to honor the achievements of the pioneers in asymmetric syntheses, the aim of this new edition was bringing the current developments, especially from younger colleagues, to the attention of students. The format of the book remained unchanged, i.e. short conceptual overviews by young leaders in their field including a short biography of the authors. The growing multidisciplinary research within chemistry is reflected in the selection of topics including metal catalysis, organocatalysis, physical organic chemistry, analytical chemistry, and its applications in total synthesis. The prospective reader of this book is a graduate or undergraduate student of advanced organic chemistry as well as the industrial chemist who wants to get a brief update on the current developments in the field.

Catalysis In Asymmetric Synthesis

Author: Vittorio Caprio
Publisher: John Wiley & Sons
ISBN: 1405190914
Size: 30.81 MB
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Written from a synthetic organic chemistry perspective, this is a highly practical and relevant text for undergraduates, postgraduates and industrial organic chemists.

Advances In Asymmetric Synthesis

Author: Alfred Hassner
Publisher: Elsevier
ISBN: 9780080551999
Size: 70.29 MB
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Enantioselective synthetic methods are not only in the forefront of chemical and pharmaceutical research but activity in this area is constantly increasing. It is stimulated by the urgency to obtain drugs or compounds of medicinal interest as single anantiomers, and the keeness to synthesize natural products in nonracemic form. This volume presents seven chapters from pioneers and authorities in this rapidly expanding field.

Principles Of Asymmetric Synthesis

Author: Robert E. Gawley
Publisher: Elsevier
ISBN: 0080914136
Size: 56.64 MB
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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, this book presents a detailed analysis of the factors that govern stereoselectivity in organic reactions. After an explanation of the basic physical-organic principles governing stereoselective reactions, the authors provide a detailed, annotated glossary of stereochemical terms. A chapter on "Practical Aspects of Asymmetric Synthesis" provides a critical overview of the most common methods for the preparation of enantiomerically pure compounds, techniques for analysis of stereoisomers using chromatographic, spectroscopic, and chiroptical methods. The authors then present an overview of the most important methods in contemporary asymmetric synthesis organized by reaction type. Thus, there are four chapters on carbon-carbon bond forming reactions, one chapter on reductions, and one on oxidations (carbon-oxygen and carbon-nitrogen bond forming reactions). This organization allows the reader to compare the leading methods for asymmetric synthesis in an appropriate context. A highlight of the book is the presentation and discussion of transition states at the current level of understanding, for important reaction types. In addition, extensive tables of examples are used to give the reader an appreciation for the scope of each reaction. Finally, leading references are provided to natural product synthesis that has been accomplished using a given reaction as a key step. Authoritative glossary to aid understanding of stereochemical terminology Explanations of the key factors influencing stereoselectivity with numerous examples, organized by reaction type A handy reference guide to the literature of asymmetric synthesis for practitioners in the field

Heterocycles In Natural Product Synthesis

Author: Krishna C. Majumdar
Publisher: John Wiley & Sons
ISBN: 3527634894
Size: 48.11 MB
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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.