Nenad Raos

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CROATICA CHEMICA ACTA 70 (2) (1997) A5Alfred Hassner (Ed.)Advances in Asymmetric SynthesisJAI Press Inc., London, 1995, Vol. 1,XII + 320 pages, 6 chapters.ISBN 1-55938-699-1This edition of JA! Press deals with synthetic procedure s for the prepa-ration of enantiomers and other molecules with asymmetric carbon atoms.These methods have become very popular in recent times because every che-mist who deals with the synthesis of natural product needs them. Like othereditions of the JAI Press, this book is aimed mainly at graduate studentsand postdoctoral fellows.In the first chapter (44 pages, 94 references), written by K. Mikami (To-kyo Institute of Technology), asymmetric carbonyl-ene reaction is describedwhich yields a stereochemically pure product up to 100% (> 99%), especiallywhen reactants in the form of trimethylsilyl derivatives and reagents likeSnC14and EtAlCb are employed. The use of these synthetic procedures inpreparations of of a-amino acids, p-amino alcohols, cholesterol and otherpharmacologically interesting compounds are described, and the mechanismof the reaction is discussed referring to the results of X-ray analysis.The chapter (50 pages, 54 references) written by R. M. Williams (Colo-rado State University) is devoted to asymmetric synthesis of a-amino acids.After ashort overview of six categories of methods for the asymmetric syn-thesis of amino acids, the author in five subsequent paragraphs describesthe preparation of optically active glycinates, electrophilic glycinates, deri-vatives of 1-aminocyclopropane-1-carboxylic acid, glycine enolates and theuse of asymmetric (1,3)-dipolar cycloadditions in the synthesis of amino ac-ids with highly substituted pyrrolidine carboxylic acid ring systems. It is in-teresting to note that nearly all of these synthetic procedures gave enantio-meric excess (ee) > 99%.1. Ojima (State University of New York at Stony Brook) wrote the chap-ter on asymmetric synthesis by means of the p-lactam synthon method. Thissynthesis, which starts from cleavage of N-C4 bond in p-lactam skeleton,was used for the synthesis of n-amino acids (especially a-alkyl-a-amino ac-ids) and their derivatives, oligopeptides, labeled peptides, polyamines, poly-A6 CROATICA CHEMICA ACTA 70 (2) (1997)amino alcohols and polyamino ethers. The author and his group developed,,~-Lactam Synthon Method- (~-LSM) for polypeptide synthesis which wasused for synthesis of enkefalin. The enantiomeric excess of the reaction var-ied, but usually reached 99%.H. C. Brown and P. V. Ramachandran (Purdue University, Indiana) de-voted their article (63 pages, 178 references) to the asymmetric synthesesvia organoboranes, the research field which »is now so large that it is nolonger possible to review them completely in a chapter such as this«, butthey concentrated only on the derivatives of u-pinene, namely on diisopino-camphenylborane and monoisopinocamphenylborane. These reagents are soefficient that the other reagents prepared from terpenes were used only forcomparative purposes. The syntheses of loganin, Corey-lactone intermediatefor prostaglandin synthesis, capsorubin (carotenoid from red paprika), andchiral aldehydes, acids, amines, olefins, acetylenes and natural products asinsect pheromones, sugars and amino acids are described.The chapter (58 pages, 83 references) written by K. Mori (University ofTokyo) is some kind of a chemist's overview of insect chemistry and thereader should not find only the interesting synthetic routes, but should ba-come familiar with the diversity and complexity of the chemistry of insecthormones, antifeedants and pheromones. Detailed syntheses of 23 naturalproducts are presented and - interesting to note - these syntheses were per-formed in order to prove the structure of the natural product (in the old-fashioned manner!) because most of them were volatile oils and, conse-quent1y, their structure could not be determined by X-ray analysis.The last chapter (41 pages, 95 refrences) is essentially a story by J. W.Reed and T. Hundlicky of the Virginia Polytechnic Institute and State Uni-versity about the application and development of the methods of enzymaticoxydation of aromatic compounds in their laboratory. The starting materialfor their syntheses were monosubstituted benzenes (mostly chlorobenzene)which were converted to cis-cyclohexadiene-1,2-diols and by the use of tolu-ene dioxigenase and similar enzymes converted to a number of natural prod-ucts, like cyclitol, inositol, carbohydrates and pinitols. At the end, they pre-sent 20 aromatic compounds synthesized by their group in 1988--1993,among which were PGE2a, specionin, conduritol and kifunesine.In my opinion, the book can help the chemist in designing the syntheses,but should be interesting to everybody wanting to know what can be ob-tained by the modern methods of organic synthesis. Therefore, I recommendthe book also to biochemists, stereochemists and to all those whose interestsare not limited to their research field.Nenad Raos

Alfred Hassner (Ed.): Advances in Asymmetric Synthesis

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