Basic Concepts in Organic Stereochemistry

This book discusses essential stereochemical concepts associated with organic molecules (natural or synthetic), as reflected in the course of their many reactions, their mechanisms, their asymmetric synthesis, biosynthesis, and biological activities. This treatise provides useful insights and understanding of the chiral/achiral designations (nomenclatures), the stereochemical features, and related properties of the natural and synthetic products. Without having an adequate knowledge of stereochemical concepts, it will not be possible to understand and appreciate the stereochemistry of natural or synthetic products. Thus, essential static and dynamic aspects of stereochemistry with sufficient illustrative examples along with discussions are presented. The structure of the monograph allows for easy selection of separate topics for reading and teaching. This book will also provide an idea of basic stereochemical concepts, as applied to organic molecules in general as well as to organic ligands in coordination complexes, and will, therefore, be valuable resources to teachers and students of advanced undergraduates and post-graduates, researchers, and professionals.

Autorentext

Professor Sunil Kumar Talapatra has taught stereochemistry, conformational analysis, reaction mechanisms and alkaloids in the postgraduate classes of Calcutta University and Presidency College (now University), Kolkata, and has been a Guest teacher in stereochemistry in universities of W. Bengal and Tripura for more than three decades. He conducted his PhD (CU) and post-doctoral work with Professor (Mrs) Asima Chatterjee and then further post-doctoral work (4 yr) with Professor Michael P Cava at OSU, Columbus. He was a Visiting Scientist at the Illinois U (Chicago), UCSC Santa Cruz, and UCSD San Diego. As a UNESCO Senior Visiting Scientist (1982) he was briefly associated with Professors E J Corey, K Nakanishi, H Rapoport, J Meinwald, N Takahashi, K Mori, and Y Kanaoka. He is the author of more than 175 research papers and a recipient of several awards; he was a British Council Guest Visitor (1973), took part in INSA and UGC Cultural Exchange Programmes in Hungary and Czechoslovakia and was elected CChem FRIC (London) in 1974. He is a former President of the Indian Chemical Society (2002 & 2003), currently Advisor, and has been the Senior-most Vice-President of the Indian Science News Association (since 2008). Professor Talapatra's research contributions include the discovery, structure elucidation and stereochemistry of more than 100 new bioactive secondary metabolites, isolated from medicinal plants, mostly alkaloids and terpenoids of different classes, coumarins and other oxygen heterocycles, polyphenolics, cardiac glycosides and one new C26 tetracyclic diamine from a marine sponge. He published more than 175 research papers. 25 Students obtained the PhD degree of the Calcutta University under his guidance, and he co-supervised more than 40 PhD students and post-doctoral fellows. Many of them joined Universities, IIT Kharagpore, Research Institutes, and Colleges, and pursued own teaching and research careers. Professor Talapatra was a nominator for the Nobel Prize Award in Chemistry for 1989 and 1994 (two nominees for each year). Two of the nominated scientists received Nobel Prize. Professor Bani Talapatra has taught natural products chemistry at Calcutta University for more than three decades and has been a Guest teacher in universities of W. Bengal and Tripura for more than a decade. She also taught general chemistry in a local undergraduate college for several years during her early professional career. She obtained the D.Sc. degree of the Calcutta University working in the laboratory of Professor (Mrs) Asima Chatterjee, and then joined a Postdoctoral Fellowship at the Vanderbilt University with the renowned microbiologist, Professor V. Najjar. At Vanderbilt she had the privilege of learning about organic reaction mechanism from Sir C K Ingold. As a UNESCO Senior Visiting Scientist (in 1976 and 1983) she extensively travelled and visited many major universities of USA, Europe, and Japan, and was briefly associated with Professors H. Rapoport, S Masamune, W Herz, W Parker, F Bohlmann, H. Wagner, W. Kraus and N. Takahashi. Professor Talapatra's research interests include various aspects of natural products chemistry including terpenoids, alkaloids, polyphenolics, and reaction mechanisms. She has published more than 140 research papers and 15 students have obtained a PhD degree under her guidance, and about 50 PhD students and post-doctoral fellows were co-supervised by her.

Inhalt

Symmetry and Molecular Chirality. Conformation, Stability, and Physical Properties.- Configurational Nomenclature. Physical Properties of Geometrical Isomers.- Projection (Fischer, Newman, Sawhorse) and Perspective (Flying Wedge and Zigzag) Formulas, Working out Stereoisomers.- Prochirality and Prostereoisomerism. Topicity of Ligands and Faces Nomenclature [1-5].- Asymmetric Synthesis.- Some Other Aspects of Dynamic Stereochemistry: Conformation and Reactivity.- Conformation of Saturated Six-Membered Ring Compounds.- Cyclohexanone.- Fused Ring Systems.- Stereoisomerism: Axial Chirality, Planar Chirality, (R,S) Notations Helicity.- Chiroptical Properties I: Optical Rotation. ORD, CD [1-4].- Chiroptical Properties II: Helicity Rule or Chirality Rule.