Recent Progress in the Chemical Synthesis of Antibiotics PDF
Preview Recent Progress in the Chemical Synthesis of Antibiotics
Gabor Lukacs . Masaji Ohno (Ed.) Recent Progress in the Chemical Synthesis of Antibiotics With 170 Illustrations Springer-Verlag Berlin Heidelberg NewY ork London Paris Tokyo Hong Kong Barcelona Dr. G. Lukacs Directeur de Recherche C.N.R.S. Institut de Chimie des Substances Naturelles du C.N.R.S. Avenue de la Terrasse F-91198 Gif-sur-Yvette Cedex, France Prof. Dr. M. Ohno University of Tokyo 7-3-1 Hongo, Bunkyo-ku Tokyo 113, Japan ISBN-13: 978-3-642-75619-1 e-ISBN-13: 978-3-642-75617-7 001: 10.1007/978-3-642-75617-7 Library of Congress Cataloging-in-Publication Data Recent progress in the chemical synthesis of antibiotics/ Gabor Lukacs, Masaji Ohno (ed.). Includes index. ISBN-13: 978-3-642-75619-1 (U.S.) 1. Antibiotics - Synthesis. 2. Pharmaceutical chemistry. 3. Organic compounds - Synthesis. I. Lukacs, Gabor, 1937- II. Ohno, Masaji, 1930- [DNLM: 1. Antibiotics - chemical synthesis. QV 350 R2958] RS431.A6R43 1990 615'.329 - dc20 DNLMjDLC This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, re-use of illustrations, recitation, broadcasting, reproduction on microfilms or in other ways, and storage in data banks. Duplication of this publication or parts thereof is only permitted under the provision of the German Copyright Law of September 9,1965, in its current version, and a copyright fee must always be paid. Violations fall under the prosecution act of the German Copyright Law. © Springer-Verlag Berlin Heidelberg 1990 Softcover reprint of the hardcover 1st edition 1990 The use of registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. 2151/3020-543210 Printed on acid-free paper. Foreword The use of antibiotics in the treatment by antibacterial and antifungal chemo therapy, has become standard practice since the end of World War Two and has had an enormous impact on healthcare throughout the world. Compounds belonging to this class have also reached an important place in the medical treatment of human cancer. Although, the discovery of most of these agents came from more or less sophisticated screening programs of soil microrganisms, many of the important antibiotics used today in clinical practice are derived from the original biosynthetic products by the application of often novel and generally elaborated chemical synthetic methodologies. In fact the antibiotics have represented (and still represent) for a generation of organic chemists an endless source of molecular structures whose varied assemblage of carbon atom backbones and chemical functions was beyond any possibility of imagination. Perhaps a similar repertoire of chemotypes was formerly offered by the natural products, namely the alkaloids, the terpenes, the vitamins and hormones as well as the pigments of the animal and plant kingdoms, albeit the chemical arrange ments of the antibiotic molecules appeared much more surprising and diverse to the admiring eyes of cultivated organic chemists. The idea of this book, certainly a landmark in the field, came during the Symposium of EUCHEM on Chemical Synthesis of Antibiotics, that was held at Aussois in Savoy, France (May 2-6, 1988), the initiative being taken by Gabor Lukacs to whom Masaji Ohno readily associated as a co-editor. However, contributors are not only those who attended the symposium, and the content of the book goes far beyond the program of the Aussois conference. This meeting has spawned a series of conferences, the second one of which will be held in Japan later this year whereas a third symposium will take place in Germany in 1992. In planning the book, the Editors sought major researchers involved in the chemical synthesis or manipulation of antibiotics in order to provide a compre hensive view of the chemistry of these agents. Each chapter gives an account of work done by a single research group, central issues being the synthetic strategies and the novelty of the chemical reactions without however forgetting the pharmacological significance of the targets. vi Foreword The first five chapters are concerned with the macrolides. The subjects range from the older well-established antibacterial agents belonging to this structural type to the newer antiparasitic drugs such as the avermectins and the milbemy cins, and include the ansamycins and the polyenes. The depsipeptides of the pristinamycin family are the subject of the sixth chapter. Subsequently we go through the updating chapter on the quinolones to the one describing brilliant chemistry on actinobolin and bactinobolin, another example of the opportun ities that the antibiotics offer to the "maestri" of the contemporary art of synthetic organic chemistry. Then follow the chapters on major drugs such as the nucleosides and lincomycin, and the one on the rationally designed antican cer agents based on the bleomycin mechanism of action. Here we have an illuminating example of the new approach, based on molecular engineering, aimed at improving the affinity for the receptor site. Four other families of antibiotics are dealt with in chapters 12 through 15, namely the mitomycins, the polyethers, the anthracyclines and related antibiotics, all contributions being presented by well known experts in the fields. Finally the last five chapters, all concerned with the brightest (since the fundamental contribution of E.B. Chain) stars of the antibiotic firmament, the beta lactams. These outstanding chemicals are presented in their diversity embracing a wide range of creative efforts and elegant synthetic complexity. Small molecules are more beautiful in this case? Not necessarily so. These final chapters do not need any comment, they must be read. I trust that this book will provide an up-to-date account of the chemistry of most important antibiotics. It is hoped that the readers will be stimulated to explore further this synthetic field that, even in these times in which so great attention is paid by the medicinal chemists to exciting issues like molecular recognition and computer aided drug design, still proves intellectually fulfilling and is endowed with industrial priority. June, 1990 Federico Arcamone Table of Contents Total Synthesis of Macrolide Antibiotics K. Tatsuta . ................. . 1 Structural Modification of Macrolide Antibiotics H. Kirst . ............ . 39 Av ermectins and Milbemycins T. Blizzard, M. Fisher, H. Mrozik, T. Shih .. 65 Ansamacrolides M. Isobe . .... 103 Polyene Macrolides: Stereostructural Elucidation and Synthetic Studies of a Few Members J.-M. Beau ..................................... 135 The Chemistry of Pristinamycins J.-M. Paris, J.-e. Barriere, e. Smith, P.-E. Bost. 183 Recent Advances in the Chemistry of Quinolones D. Bouzard ...................... . 249 Actinobolin and Bactobolin: Chemical Aspects and Syntheses B. Fraser-Reid, J.e. Lopez ..................... . 285 Nucleosides: Potential Drugs for AIDS Therapy F. De las Heras, M.-J. Camarasa, J.-M. Fiandor . . .......... 321 Total Synthesis of Lincomycin and Related Chemistry A. Golebiowski, J. Jurczak ................ . 365 Synthetic Study on Man-Made BleQmycins Based on the Anticancer Mechanism of Natural Bleomycins M. Ohno, M. Otsuka. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 387 Synthesis of Mitomycins W.A. Remers, B. Iyengar 415 viii Table of Contents Total Synthesis of Polyether Antibiotics O. Yonemitsu, K. Horita . .......... . 447 Synthesis of Anthracyclines Related to Daunomycin G.J. Thomas . ................... . 467 Synthesis of Polynuclear Aromatic Antibiotics A. V. Rama Rao . ..................... . 497 Synthetic Aspects of Monocyclic ~-Lactam Antibiotics R.C. Thomas ........................ . 533 Recent Advances in the Synthesis of PS-5 and PS-6 Antibiotics and Related Carbapenem Compounds C. Palomo. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 565 Synthesis of Penems E. Perrone, G. Franceschi .. 613 1-0xacephem Antibiotics M. Narisada, T. Tsuji . ..................... . 705 Non-~-Lactam Analogs of Penicillins and Cephalosporins J. Marchand-Brynaert, L. Ghosez 727 Subject Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 795 List of Authors Jean-Claude Barriere, Rhone-Poulenc Sante, Centre de Recherches de Vitry-Alfortville, 13, quai Jules Guesde, F-94403 Vitry sur Seine Cedex, France Jean-Marie Beau, Universite d'Orleans, Laboratoire de Biochimie Structurale, Unite Associee 499 du CNRS, BP 6759, F-45067 Orleans Cedex 2, France Timothy A. Blizzard, Merck Sharp and Dohme Research Laboratory, P.O. Box 2000, Rahway, New Jersey 07065, USA Pierre-Etienne Bost, Rhone-Poulenc Sante, Centre de Recherches de Vitry-Alfortville, 13, quai Jules Guesde, F-94403 Vi try sur Seine Cedex, France Daniel Bouzard, Bristol-Myers S.A., Research Laboratories, BP 62, F-77422 Marne La Vallee Cedex 2, France Maria-Jose Camarasa, Instituto de Quimica Medica, Juan de la Cierva 3, 28006 Madrid, Spain Jose-Maria Fiandor, Instituto de Quimica Medica, Juan de la Cierva 3, 28006 Madrid, Spain Michael H. Fisher, Merck Sharp and Dohme Research Laboratory, P.O. Box 2000, Rahway, New Jersey 07065, USA Giovanne Franceschi, Farmitalia Carlo Erba, Infectious Diseases Department, 1-20146 Milano, Italy Bertram O. Fraser-Reid, Department of Chemistry, Paul M. Gross Chemical Laboratory, Duke Univer sity, Durham, North Carolina 27706, USA x List of Authors Leon Ghosez, Universite Catholique de Louvain, Laboratoire de Chimie Organique de Syn these, Place Louis Pasteur 1, B-1348 Louvain-La-Neuve, Belgium Adam Golebiowski, Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warszawa, Poland Federico Gomez De las Heras, Instituto de Quimica Medica, Juan de la Cierva 3, 28006 Madrid, Spain Kiyoshi Horita, Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan Minoru Isobe, Laboratory for Organic Chemistry, Faculty of Agriculture, Nagoya University, Chikusa-ku, Nagoya 464, Japan Bhashyam S. Iyengar, Department of Pharmaceutical Sciences, University of Arizona, Tucson, Arizona 85721, USA Janusz Jurczak, Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warszawa, Poland Herbert A. Kirst, Fermentation Products Res. Div., Lilly Research Laboratories, Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, USA J. Cristobal Lopez, Department of Chemistry, Paul M. Gross Chemical Laboratory, Duke Univer sity, Durham, North Carolina 27706, USA Jacqueline Marchand-Brynaert, Universite Catholique de Louvain, Laboratoire de Chimie Organique de Syn these, Place Louis Pasteur 1, B-1348 Louvain-La-Neuve, Belgium Helmut Mrozik, Merck Sharp and Dohme Research Laboratory, P.O. Box 2000, Rahway, New Jersey 07065, USA Masayuki Narisada, Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553,Japan List of Authors xi Masaji Ohno, Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan Masami Otsuka, Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan Claudio Palomo, Departmento de Quimica Aplicada, Unidad de Quimica Organica, Facultad de Ciencias Quimicas, Universidad de Pais Vasco, Apdo. 1072, 20080 San Sebastian, Spain Jean-Marc Paris, Rhone-Poulenc Sante, Centre de Recherches de Vitry-Alfortville, 13, quai Jules Guesde, F-94403 Vitry sur Seine Cedex, France Ettore Perrone, Farmitalia Carlo Erba, Infectious Diseases Department, 1-20146 Milano, Italy A.V. Rama Rao, Indian Institute of Chemical Technology, Hyderabad 500 007, India Willian Alan Remers, Department of Pharmaceutical Sciences, University of Arizona, Tucson, Arizona 85721, USA Thomas L. Shih, Merck Sharp and Dohme Research Laboratory, P.O. Box 2000, Rahway, New Jersey 07065, USA Christopher Smith, Rhone-Poulenc Ltd., Dagenham Research Centre, Rainham Road South, Dagenham, Essex RMI0 7XS, United Kingdom Kuniaki Tatsuta, Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku, Yokohama 223, Japan Gareth John Thomas, Research Division, Roche Products Limited, P.O. Box 8, Welwyn Garden City, Hertfordshire AL 7 3A Y, United Kingdom Richard C. Thomas, Cancer and Infectious Diseases Research, The Upjohn Company, Kalamazoo, MI 49001, USA
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