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The purpose of this book is to review and critically evaluate the best new methods to synthesize alpha-amino acids in optically active form. There is so much new literature on amino acid synthesis that the experimentalist will undoubtedly have difficulty in selecting the most appropriate methodology for constructing the amino acid of immediate interest. This book is a guide for steering the scientist through the maze of existing reports on the subject and contains the most up-to-date critical reviews of methods of asymmetric synthesis of amino acids. In areas that are relatively new conceptually and less studied experimentally, an effort has been made to review the most salient works with an eye towards future development. Over 330 schemes and figures are presented with references for rapid visual retrieval of information. The book will be of great value to academic and industrial organic research chemists, especially those concerned with medicinal and agricultural chemistry, as well as to graduate and post graduate students, biochemists and biologists.
This work provides a comprehensive overview of, and the most common and useful methods for, the synthesis of non-alpha-amino acids, particularly amino acids that are key synthetic intermediates or important compounds in their own right. Attention is paid to acyclic amino acids C3-C10 including amino alkanoic carboxylic acids, aminoalkenoic acids and aminoalkynoic acids.
The purpose of this book is to review and critically evaluate the best new methods to synthesize alpha-amino acids in optically active form. There is so much new literature on amino acid synthesis that the experimentalist will undoubtedly have difficulty in selecting the most appropriate methodology for constructing the amino acid of immediate interest. This book is a guide for steering the scientist through the maze of existing reports on the subject and contains the most up-to-date critical reviews of methods of asymmetric synthesis of amino acids. In areas that are relatively new conceptually and less studied experimentally, an effort has been made to review the most salient works with an eye towards future development. Over 330 schemes and figures are presented with references for rapid visual retrieval of information. The book will be of great value to academic and industrial organic research chemists, especially those concerned with medicinal and agricultural chemistry, as well as to graduate and post graduate students, biochemists and biologists.
This volume presents the most recent and comprehensive collection of reviews on methodological developments in the field of alpha-amino acids.
Although less common than α-amino acids, non-α-amino acids—where the amino group is not on the carbon immediately adjacent to the carboxyl group but is attached to another carbon in the chain (for example, the β, γ, δ carbon)—are components of biologically important molecules, are significant in the pharmaceutical industry, and are useful starting materials for many areas of organic chemistry. Since the publication of the first edition of this book nearly 20 years ago, synthetic work devoted to the preparation of non- α-amino acids has expanded greatly. Methods of Non-α-Amino Acid Synthesis, Second Edition has been extensively rewritten and reorganized, providing an up-to-date review of strategies and methods for non-α-amino acid synthesis, particularly those amino acids that are key synthetic intermediates or important compounds in their own right. It focuses on acyclic amino acids of C3–C10, but also aminoalkanoic carboxylic acids, aminoalkenoic acids, and aminoalkynoic acids. The new edition contains many updated references and has a greater emphasis on the biological importance of non-α-amino acids. In addition to an array of synthetic methods, the book offers discussions on why non-α-amino acids are important. The book covers synthetic methods that rely on substituent refunctionalization, the conversion of cyclic precursors to acyclic amino acids, conjugate addition reactions, and enolate anion reactions and condensation reactions that lead to non-α-amino acids. It also examines reactions and strategies that lead to good diastereoselectivity and enantioselectivity during synthesis. A chapter devoted to biologically important amino acids includes separate sections on GABA, GABOB, carnitine, DAVA, statine, and other significant amino acids as well as a new section on peptides and proteins that contain non-α-amino acids. The final chapter addresses aminocyclic and heterocyclic amino acids.
New general methodology for the stereoselective synthesis of unnatural alpha-amino acids has been developed. Early work focussed on investigating methods for the generation of chiral allylic alcohols using cross-metathesis of a simple enone with various terminal alkenes, followed by an asymmetric ketone reduction. The allylic alcohols were then converted to protected allylic amines via Overman rearrangement chemistry. Oxidative alkene cleavage and hydrolysis of these intermediates generated a range of alpha-amino acid targets. Attempts were also made to apply the developed methodology to the synthesis of a simple alpha,alpha-disubstituted alpha-amino acid target. The Overman rearrangement was also applied to the generation of a late-stage intermediate which could be used in the synthesis of (2S,3S)-capreomycidine, a component of a number of peptides which exhibit antibacterial activity.