Asymmetric Synthesis of Natural Products

The indispensable reference for the twenty-first century chemist… A fascinating and comprehensive look into one of chemistry's fastest growing specialties–sesquiterpene synthesis–Volume Ten of The Total Synthesis of Natural Products focuses on acyclic and monocyclic compounds and sheds light on the structure and makeup of this important class of hydrocarbons. A useful and practical tool for researchers interested in locating any of the major classes of sesquiterpene compounds, the author will also provide, if needed, a database to the more than 1,600 articles on sesquiterpene synthesis. The ultimate index to the newest experimental work in synthetic chemistry, this latest volume in The Total Synthesis of Natural Products series is also a glossary to the new language of chemistry in the next century. Look for the following related title in the series: THE TOTAL SYNTHESIS OF NATURAL PRODUCTS, Volume Eleven Volume Eleven continues the authoritative coverage on sesquiterpene synthesis begun in Volume Ten, examining compounds with bicyclic and tricyclic ring structures., 1997 (0-471-18874-3) The research on the synthesis of sesquiterpenes, derivatives of terpenes, a class of hydrocarbons commonly found in oils, resins, and balsams, has grown exponentially over the past fifteen years. With over 500 sesquiterpene syntheses already developed, the literature on this experimental specialty is voluminous, now encompassing over 1,600 re-search papers. Volume Ten in The Total Synthesis of Natural Products provides a systematic and comprehensive look at acyclic and monocyclic compounds in sesquiterpene synthesis. Reflecting one of the significant changes in sesquiterpene re-search, that is, the increase in compound targets prepared in an optically active form, the present volume includes their absolute configurations, signs of optical rotation, or both. This newest volume in The Total Synthesis of Natural Products series is an «A-to-Z» look at acyclic and monocyclic compounds in sesquiterpene synthesis, one of the most dynamic areas in the ongoing revolution in chemical synthesis, and is a must for the chemical professional.

For chemists, attempting to mimic nature by synthesizing complex natural products from raw material is a challenge that is fraught with pitfalls. To tackle this unique but potentially rewarding task, researchers can rely on well-established reactions and methods of practice, or apply their own synthesis methods to verify their potential. Whatever the goal and its complexity, there are multiple ways of achieving it. We must now establish a strategic and effective plan that requires the minimum number of steps, but lends itself to widespread use. This book is structured around the study of a dozen target products (butyrolactone, macrolide, indole compound, cyclobutanic terpene, spiro- and polycyclic derivatives, etc. ). For each product, the different disconnections are presented and the associated syntheses are analyzed step by step. The key reactions are described explicitly, followed by diagrams showing the range of impact of certain transformations. This set of data alone is conducive to understanding syntheses and indulging in this difficult, but worthwhile activity.

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.

Here, all aspects of the topic are presented in a compact manner. The book is clearly structured, and divided into two sections – asymmetric synthesis of heterocycles containing only one nitrogen and that of those with more than one nitrogen as a heteroatom – such that the necessary information may be found at a glance. The international team of authors provides important experimental procedures, including industrial applications. Essential for synthetic chemists in pharmaceutical and agrochemical chemistry.

Authored by two internationally recognized experts with an excellent track record, this much-needed reference summarizes latest research in the rapidly developing field of stereoselective synthesis of enantiomerically enriched amino acids, particularly of non-proteinogenic origin. It highlights several different catalytic and stoichiometric asymmetric methods for their synthesis and also provides information on origin, biological properties, different synthetic strategies and important applications in medicine and pharmacology. Essential reading for synthetic chemists working in the field of asymmetric synthesis, natural products and peptide synthesis, stereochemistry, medicinal chemistry, biochemistry, pharmacology, and biotechnology.

From the reviews of the First Edition . . . «An excellent text . . . will no doubt provide the benchmark for comparative works for many years.» —Journal of the American Chemical Society «A resounding success . . . the definitive current summaries on their respective subjects.» —Synthesis Since this important work was first published in 1993, the field of catalytic asymmetric synthesis has grown explosively, spawning effective new methods for obtaining enantiomerically pure compounds on a large scale and stimulating new applications in diverse fields-from medicine to materials science. Catalytic Asymmetric Synthesis, Second Edition addresses these rapid changes through new or substantially revised contributions from highly recognized world leaders in the field. It presents detailed accounts of the most important catalytic asymmetric reactions known today, discusses recent advances, and retains from the previous edition essential and intriguing information on the initial development of certain processes. An excellent working resource for academic researchers and industrial chemists alike, the Second Edition features: Contributions from Noyori, Sharpless, Kagan, Trost, Overman, Shibasaki, Doyle, Okamoto, Bolm, Carreira, and many other internationally renowned authorities New chapters on asymmetric carbometallations, asymmetric amplification and autocatalysis, and asymmetric polymerization Extended coverage of asymmetric carbene reactions, including asymmetric intramolecular carbene insertion to C-H bonds as well as asymmetric dihydroxylation and aminohydroxylation Extended coverage of asymmetric carbon-carbon bond-forming reactions and applications An appendix listing all chiral ligands in the book

Praise for the previous editions «An excellent text . . . will no doubt provide the benchmark for comparative works for many years.» —Journal of the American Chemical Society «An excellent state-of-the-art compilation of catalytic asymmetric chemistry . . . should be included in any chemistry reference collection.» —Choice «This is a tremendous resource and an excellent read. I recommend immediate purchase.» —Perkin Transactions Since this important work was first published in 1993, the field of catalytic asymmetric synthesis has grown explosively, spawning effective new methods for obtaining enantiomerically pure compounds on a large scale and stimulating new applications in diverse fields—from medicine to materials science. Catalytic Asymmetric Synthesis, Third Edition addresses these rapid changes through contributions from highly recognized world leaders in the field. This seminal text presents detailed accounts of the most important catalytic asymmetric reactions known today, and discusses recent advances and essential information on the initial development of certain processes. An excellent working resource for academic researchers and industrial chemists alike, the Third Edition features: Six entirely new chapters focusing on novel approaches to catalytic asymmetric synthesis including non-conventional media/conditions, organocatalysis, chiral Lewis and Bronsted acids, CH activation, carbon-heteroatom bond-forming reactions, and enzyme-catalyzed asymmetric synthesis A new section focusing on the important new reaction, asymmetric metathesis, in carbon-carbon bond-forming reactions Updated chapters on hydrogenation, carbon-carbon bond-forming reactions, hydrosilylations, carbonylations, oxidations, amplifications and autocatalysis, and polymerization reactions Retaining the best of its predecessors but now thoroughly up to date, Catalytic Asymmetric Synthesis, Third Edition serves as an excellent desktop reference and text for researchers and students from the upper-level undergraduates through experienced professionals in industry or academia.

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.

Authored by one of the leading experts in the field, this is the only comprehensive overview of chiral organophosphorus compounds, from asymmetric synthesis to catalysis and pharmacological applications. As such, this unique reference covers the chemical background as well as spectroscopical analysis of phosphorus compounds, and thoroughly describes all the various synthetic strategies for these substances. Metal-, organo- and biocatalyzed reactions for the introduction of phosphorus are explained as are asymmetric oxidation and reduction methods for the preparation of all possible oxidation states of phosphorus. The text also includes industrial applications for these compounds. Of particular interest to chemists working in the field of asymmetric synthesis, as well as to the pharmaceutical industry due to the increasing number of phosphorous-containing drugs.

Current discoveries and research into bioactive natural products Medicinal Chemistry of Bioactive Natural Products provides a much-needed survey of bioactive natural products and their applications in medicinal chemistry. This comprehensive reference features articles by some of the world's leading scientists in the field on discovery, structure elucidation, and elegant synthetic strategies–developed for natural products–with an emphasis on the structure activity relationship of bioactive natural products. The topics have been carefully chosen on the basis of relevance to current research and to importance as clinicially useful agents. Rather than attempting to be a comprehensive encyclopedia of bioactive natural products, Medicinal Chemistry of Bioactive Natural Products guides the reader to the key developments in the field. By providing not only practical detail but a historical perspective on the chemistry and biology of the compounds under consideration, the book serves as a handy resource for researchers in their own work developing pharmaceuticals, and as an inspiring introduction for young scientists to the dynamic field of bioactive natural products research. Enhanced by examples with updated research results, the discussion covers such topics as: * The chemistry and biology of epothilones * Vancomycin and other glycopeptide antibiotic derivates * Antitumor and other related activities of Taxol and its analogs * The antimalarial properties of the traditional Chinese medicine, Quinghaosu (artemisinin) * Huperzine A: A natural drug for the treatment of Alzheimer's disease * The medicinal chemistry of ginkgolides from Ginkgo biloba * Recent progress in Calophyllum coumarins as potent anti-HIV agents * Plant-derived anti-HIV agents and analogs * Chemical synthesis of annonaceous acetogenins and their structurally modified mimics