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Natural Lactones and Lactams Related Titles Edited by Tomasz Janecki Natural Lactones and Lactams Related Titles Dinges, J., Lamberth, C. (eds.) Pozharskii, A. F., Soldatenkov, A., Katritzky, A. R. Bioactive Heterocyclic Compound Heterocycles in Life and Society Classes An Introduction to Heterocyclic Chemistry, Biochemistry and Applications Pharmaceuticals Second Edition 2012 2011 ISBN: 978-3-527-33395-0 ISBN: 978-0-470-71410-2 (Also available in digital formats) (Also available in digital formats) Lamberth, C., Dinges, J. (eds.) Anderson, R.R., Groundwater, P.P., Todd, A.A., Bioactive Heterocyclic Compound Worsley, A.A. Classes Antibacterial Agents – Chemistry, Agrochemicals Mode of Action, Mechanisms of 2012 Resistance and Clinical ISBN: 978-3-527-33396-7 Applications (Also available in digital formats) 2012 Hanessian, S., Giroux, S., Merner, B.L. ISBN: 978-0-470-97244-1 (Also available in digital formats) Design and Strategy in Organic Synthesis Diana, P., Cirrincione, G. From the Chiron Approach to Catalysis Biosynthesis of Heterocycles 2013 2013 ISBN: 978-3-527-33391-2 ISBN: 978-1-118-02867-4 Eicher, T., Hauptmann, S., Speicher, A. Yudin, A.K. (ed.) The Chemistry of Heterocycles Catalyzed Carbon-Heteroatom Structure, Reactions, Synthesis, and Applications Bond Formation Third Edition 2011 2012 ISBN: 978-3-527-32428-6 ISBN: 978-3-527-32868-0 (Also available in digital formats) Majumdar, K.C., Chattopadhyay, S.K. (eds.) Heterocycles in Natural Product Synthesis 2011 ISBN: 978-3-527-32706-5 (Also available in digital formats) Edited by Tomasz Janecki Natural Lactones and Lactams Synthesis, Occurrence and Biological Activity The Editor All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the Prof. Tomasz Janecki information contained in these books, Lodz University of Technology including this book, to be free of errors. Department of Chemistry Readers are advised to keep in mind that Institute of Organic Chemistry statements, data, illustrations, procedural Z˙ eromskiego 116 details or other items may inadvertently be 90-924 Łod´ z´ inaccurate. Poland Library of Congress Card No.: applied for British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library. Bibliographic information published by the Deutsche Nationalbibliothek The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at <http://dnb.d-nb.de>. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Boschstr. 12, 69469 Weinheim, Germany All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Print ISBN: 978-3-527-33414-8 ePDF ISBN: 978-3-527-66694-2 ePub ISBN: 978-3-527-66693-5 Mobi ISBN: 978-3-527-66692-8 oBook ISBN: 978-3-527-66691-1 Cover Design Simone Benjamin, Blue Sea Design, McCleese Lake, Canada Typesetting Laserwords Private Limited, Chennai, India Printing and Binding Markono Print Media Pte Ltd, Singapore Printed on acid-free paper V Contents Preface XIII List of Contributors XV 1 Tetronic Acids 1 Dimitris Georgiadis 1.1 Introduction 1 1.2 Natural Occurrence, Biological Activities, and Biosynthesis 1 1.3 5-Ylidene Tetronic Natural Products 6 1.3.1 Pulvinic Acids and Pulvinones 6 1.3.2 Agglomerins 11 1.3.3 Tetronomycin 13 1.3.4 Stemofoline Alkaloids 13 1.3.5 Variabilin 17 1.3.6 Tetrodecamycin 17 1.4 5-Monosubstituted Tetronic Natural Products 19 1.4.1 Carlic, Carlosic, Carolic, Carolinic, and Viridicatic Acids 19 1.4.2 RK-682 20 1.4.3 Massarilactone B 21 1.4.4 Annularins F, G, and H 21 1.4.5 Palinurin 23 1.4.6 Pesthetoxin 24 1.4.7 Rotundifolides A and B 24 1.5 5-Disubstituted Tetronic Natural Products 25 1.5.1 5-Dialkyl Tetronic Natural Products 25 1.5.1.1 Vertinolide 25 1.5.1.2 Papyracillic Acid B 26 1.5.1.3 Bisorbibutenolide 26 1.5.2 5-Spirotetronic Natural Products 29 1.5.2.1 Spirotetronic Antibiotics 29 1.5.2.2 Ircinianin and Wistarin 35 1.5.2.3 Stemonamine Alkaloids 35 1.5.2.4 Abyssomicins 37 1.6 5-Unsubstituted Tetronic Natural Products 41 VI Contents 1.6.1 Tetronasin 41 1.7 Conclusions 42 References 43 2 Recent Advances in the Field of Naturally Occurring 5,6-Dihydropyran-2-ones 51 Juan Alberto Marco and Miguel Carda 2.1 Introduction 51 2.2 Synthetic Methodologies for 5,6-Dihydropyran-2-ones 52 2.2.1 Lactonization of Substituted δ-Hydroxy Acid Derivatives 52 2.2.2 Oxidation of Substituted Dihydropyran Derivatives 53 2.2.3 Ring-Closing Metathesis 54 2.2.4 Miscellaneous Methods 54 2.3 Formation of Stereogenic Centers inside the Dihydropyrone Ring 55 2.3.1 Use of Chiral Precursors 56 2.3.1.1 Carbohydrate and Related Precursors 56 2.3.1.2 Chiral Hydroxy Acids 58 2.3.1.3 Chiral Epoxides 60 2.3.1.4 Other Chirons 62 2.3.2 Asymmetric (Enantioselective) Reactions 64 2.3.2.1 Asymmetric (Enantioselective) Sharpless Epoxidations or Dihydroxylations 64 2.3.2.2 Asymmetric Aldol-Type Reactions 68 2.3.2.3 Asymmetric Allylations 69 2.3.2.4 Asymmetric Carbonyl Reductions 71 2.3.2.5 Asymmetric Alkylations 72 2.3.2.6 Asymmetric Epoxide Hydrolysis 73 2.3.2.7 Asymmetric Cycloadditions 74 2.3.2.8 Other Asymmetric Methods 75 2.4 Pharmacological Properties of Pyrones 78 2.5 Biosynthetic Formation of Pyrones 79 2.6 Syntheses of Natural 5,6-Dihydropyran-2-ones Reported during the Period from 2006 to the First Half of 2012 91 References 91 3 β-Lactams 101 Girija S. Singh and Siji Sudheesh 3.1 Introduction 101 3.1.1 Biosynthesis of Penicillin and Cephalosporin 102 3.2 Monocyclic β-Lactams 103 3.2.1 Biosynthesis of Nocardicin A 104 3.2.2 Synthetic Approaches to Construct β-Lactam Ring 105 3.2.2.1 Cycloaddition Reactions 106 3.2.2.2 Cyclization Reactions 115 3.2.2.3 Miscellaneous Approaches 118 Contents VII 3.2.3 Biological Activity of Monocyclic 2-Azetidinones 119 3.3 Penams 121 3.3.1 Synthetic Approaches to Penam Skeleton 121 3.3.2 Biological Activity of Penams 122 3.4 Cephalosporins 124 3.4.1 Synthetic Approaches to Cephalosporin Skeleton 125 3.4.2 Biological Activity of Cephalosporins 128 3.5 Clavulanic Acid 130 3.5.1 Synthetic Approaches to Clavam Skeleton 131 3.5.2 Biological Activity of Clavams 132 3.6 Carbapenems 133 3.6.1 Synthetic Approaches to Carbapenem Skeleton 134 3.6.2 Biological Activity of Carbapenems 136 3.7 Spiro-Fused β-Lactams 137 3.7.1 Occurrence and Structure of Chartellines 137 3.7.2 Total Synthesis of Chartelline C 137 3.7.3 Biological Activity of Spiro-Fused β-Lactams 140 3.8 Summary 140 References 141 4 α-Alkylidene-γ-andδ-Lactones and Lactams 147 Łukasz Albrecht, Anna Albrecht, and Tomasz Janecki 4.1 Introduction 147 4.2 Occurrence, Biosynthesis, and Biological Activities of α-Alkylidene γ-andδ-Lactones and Lactams 148 4.2.1 α-Alkylidene-γ-Lactones 148 4.2.2 α-Alkylidene-δ-Lactones 152 4.2.3 α-Alkylidene-γ-andδ-Lactams 153 4.3 Recent Advances in the Synthesis of α-Alkylidene-γ-andδ-Lactones and Lactams 153 4.3.1 Cyclization of 2-Alkylidene-4-(5-)Hydroxyalkanoates and 2-Alkylidene-4-(5-)Aminoalkanoates in the Synthesis of α-Alkylidene-γ-andδ-Lactones and Lactams 154 4.3.1.1 Organometallic Reagents Derived from 2-Bromomethylacrylic Acid and Its Derivatives in the Synthesis of 2-Alkylidene- 4-Hydroxyalkanoates and 2-Alkylidene-4-Aminoalkanoates 155 4.3.1.2 Application of Allylboronates in the Synthesis of 2-Alkylidene- 4-Hydroxyalkanoates and 2-Alkylidene-4-Aminoalkanoates 156 4.3.1.3 Baylis–Hillman Alcohol Derivatives in the Synthesis of α-Alkylidene γ-andδ-Lactones and Lactams 161 4.3.1.4 Ring-Opening Reactions in the Synthesis of 2-Alkylidene- 4-Hydroxyalkanoates and 4-Aminoalkanoates 167 4.3.2 Construction of α-Alkylidene-γ-andδ-Lactone and Lactam Rings via Intramolecular Morita–Baylis–Hillman Reaction 168 VIII Contents 4.3.3 Methods Involving α-Dialkoxyphosphoryl-γ-andδ-Lactones and Lactams as Key Intermediates 172 4.3.3.1 Methods Involving Cyclic α,β-Unsaturated Precursors 172 4.3.3.2 Methods Involving 2-Dialkoxyphosphoryl 4-(5-)Hydroxy or 4-(5-)Aminoalkanoates as Key Intermediates 174 4.3.3.3 α-Diethoxyphosphoryl-δ-Lactones in the Synthesis of 3-Methylene-3,4-Dihydrocoumarins 182 4.3.3.4 Annulation of the Lactone Frameworks via Carbon–Carbon Bond-Forming Reactions 184 4.3.4 β-Elimination Reaction in the Synthesis of α-Alkylidene-γ-Lactones or γ-Lactams 184 4.3.5 Oxidation of 3-Alkylidenetetrahydrofuranones in the Synthesis of α-Alkylidene-γ-Lactones 186 4.3.6 Miscellaneous Methods for the Preparation of α-Alkylidenelactones and Lactams 187 4.4 Conclusions 188 References 188 5 Medium-Sized Lactones 193 Isamu Shiina and Kenya Nakata 5.1 Introduction 193 5.1.1 Natural Eight- and Nine-Membered Lactones 193 5.1.2 Lactonization Methods 194 5.1.2.1 Corey–Nicolaou S-Pyridyl Ester Lactonization Method 195 5.1.2.2 Mukaiyama Onium Salt Method 195 5.1.2.3 Masamune Thioester Activation Method 197 5.1.2.4 Yamaguchi Mixed-Anhydride Method 198 5.1.2.5 Mitsunobu Alcohol Activation Method 199 5.1.2.6 Keck–Steglich DCC/DMAP·HCl Activation Method 199 5.1.2.7 Shiina Benzoic Anhydride Method 200 5.2 Total Synthesis of Eight-Membered Lactones 203 5.2.1 Cephalosporolide D 203 5.2.1.1 Shiina Total Synthesis (1988) 203 5.2.1.2 Buszek Total Synthesis (2001) 204 5.2.1.3 Rao Total Synthesis (2010) 204 5.2.1.4 Sabitha Total Synthesis (2011) 205 5.2.2 Octalactins
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