asymmetric synthesis of natural products

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Asymmetric Synthesis Of Natural Products

Author : Ari M. P. Koskinen
ISBN : 9781118347331
Genre : Science
File Size : 24. 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 Natural Products

Author : Ari M. P. Koskinen
ISBN : 1119976685
Genre : Science
File Size : 48. 79 MB
Format : PDF, Kindle
Download : 470
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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
ISBN : 1138033618
Genre :
File Size : 79. 68 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.

Principles Of Asymmetric Synthesis

Author : Robert E. Gawley
ISBN : 9780080448602
Genre : Science
File Size : 84. 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 (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. 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

Principles And Applications Of Asymmetric Synthesis

Author : Guo-Qiang Lin
ISBN : 9780471465249
Genre : Science
File Size : 40. 36 MB
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Asymmetric synthesis remains a challenge to practicing scientists as the need for enantiomerically pure or enriched compounds continues to increase. Over the last decade, a large amount of literature has been published in this field. Principles and Applications of Asymmetric Synthesis consolidates and evaluates the most useful methodologies into a one-volume resource for the convenience of practicing scientists and students. Authored by internationally renowned scientists in the field, this reliable reference covers more than 450 reactions and includes important stoichiometric as well as catalytic asymmetric reactions. The first chapter reviews the basic principles, common nomenclature, and analytical methods, and the remainder of the book is organized according to reaction type. The text examines such topics 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 other cyclizations Applications to the total synthesis of natural products Use of enzymes in asymmetric synthesis Practicing chemists in the pharmaceutical, fine chemical, and agricultural professions as well as graduate students will find that Principles and Applications of Asymmetric Synthesis affords comprehensive and current coverage.

Copper Catalyzed Asymmetric Synthesis

Author : Alexandre Alexakis
ISBN : 9783527664597
Genre : Science
File Size : 63. 79 MB
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This book reflects the increasing interest among the chemical synthetic community in the area of asymmetric copper-catalyzed reactions, and introduces readers to the latest, most significant developments in the field. The contents are organized according to reaction type and cover mechanistic and spectroscopic aspects as well as applications in the synthesis of natural products. A whole chapter is devoted to understanding how primary organometallics interact with copper to provide selective catalysts for allylic substitution and conjugate addition, both of which are treated in separate chapters. Another is devoted to the variety of substrates and experimental protocols, while an entire chapter covers the use on non-carbon nucleophiles. Other chapters deal with less-known reactions, such as carbometallation or the additions to imines and related systems, while the more established reactions cyclopropanation and aziridination as well as the use of copper (II) Lewis acids are warranted their own special chapters. Two further chapters concern the processes involved, as determined by mechanistic studies. Finally, a whole chapter is devoted to the synthetic applications. This is essential reading for researchers at academic institutions and professionals at pharmaceutical or agrochemical companies.

The Asymmetric Synthesis Of 1 4 Benzodioxane Lignan Natural Products

Author : Lisa Ivy Pilkington
ISBN : OCLC:935877412
Genre : Amines
File Size : 83. 24 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.

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