35 Topics in Heterocyclic Chemistry

Transcription

1 35 Topics in Heterocyclic Chemistry Series Editors B.U.W. Maes, Antwerpen, Belgium Janine Cossy, Paris, France Slovenko Polanc, Ljubljana, Slovenia Editorial Board: D. Enders, Aachen, Germany S.V. Ley, Cambridge, UK G. Mehta, Bangalore, India K.C. Nicolaou, La Jolla, CA, USA R. Noyori, Hirosawa, Japan L.E. Overmann, Irvine, CA, USA A. Padwa, Atlanta, GA, USA For further volumes:

2 Aims and Scope The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field.

3 Janine Cossy Editor Synthesis of Saturated Oxygenated Heterocycles I 5- and 6-Membered Rings With contributions by M.A. Brimble K.P. Kaliappan A.J. Moreno-Vargas K. Palanichamy M.A. Perry J.D. Rainier S.D. Rychnovsky N. Sizemore L.A. Stubbing P. Vogel

4 Editor Janine Cossy ESPCI Laboratory of Organic Chemistry Paris Cedex 05 France ISSN ISSN (electronic) ISBN ISBN (ebook) DOI / Springer Heidelberg New York Dordrecht London Library of Congress Control Number: Springer-Verlag Berlin Heidelberg 2014 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. Exempted from this legal reservation are brief excerpts in connection with reviews or scholarly analysis or material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work. Duplication of this publication or parts thereof is permitted only under the provisions of the Copyright Law of the Publisher s location, in its current version, and permission for use must always be obtained from Springer. Permissions for use may be obtained through RightsLink at the Copyright Clearance Center. Violations are liable to prosecution under the respective Copyright Law. The use of general descriptive names, registered names, trademarks, service marks, 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. While the advice and information in this book are believed to be true and accurate at the date of publication, neither the authors nor the editors nor the publisher can accept any legal responsibility for any errors or omissions that may be made. The publisher makes no warranty, express or implied, with respect to the material contained herein. Printed on acid-free paper Springer is part of Springer Science+Business Media (

5 Preface Two volumes are dedicated to the synthesis of saturated oxygenated heterocycles and consist of eight chapters covering the synthesis of 5- to 16-membered ring cyclic ethers and lactones. Rather than offer an exhaustive description of the synthesis of cyclic ethers and lactones, these volumes present methods and strategies to synthesize heterocycles and thus helping the reader to find suitable methods for obtaining a desired saturated oxygenated heterocycle. The first volume comprises five chapters and the second volume three chapters. In chapter entitled Synthesis of Substituted Tetrahydrofurans, J. D. Rainier outlines the advances that have been made during the last 10 years in the synthesis of tetrahydrofurans such as nucleophilic additions to acetals and hemiacetals, cycloadditions, oxidative cyclizations, furan reductions, Prins-pinacol cascades, ring-opening of bicyclic substrates, and nucleophilic substitutions. In chapter Synthesis of Saturated Tetrahydropyrans, S.D. Rychnovsky, M. A. Perry, and N. Sizemore review the common strategies to access tetrahydropyrans such as the formation of O1 C2, C2 C3, C3 C4, O1 C6, and C2 C3 bonds, as well as C2 functionalization of lactols and lactones. The chapter Synthesis of Saturated Six-Membered Ring Lactones by K. P. Kaliappan and K. Palanichamy describes various selected methods such as lactonization of δ-hydroxy acid derivatives, oxidation, electrophilic cyclization, intramolecular nucleophilic displacement, radical and reductive cyclizations, palladium-catalyzed lactonization, as well as carbonylation and carboxylation. The synthesis of 7-oxabicyclo[2.2.1]heptanes and derivatives is reported in the chapter Synthesis of 7-Oxabicyclo[2.2.1]heptane and Derivatives has been written by P. Vogel and A. J. Moreno-Vargas. Most of the methods, reported to access 7-oxabicyclo[2.2.1]heptanes, are Diels Alder reactions, but non-diels Alder reactions such as electrophilic cyclizations have also been included in this chapter. As 7-oxabicyclo[2.2.1]heptane derivatives can be good precursors of other oxygenated heterocycles, their ring cleavage either by cleavage of a C-O or a C-C bond have been reported. In addition, as 7-oxabicyclo[2.2.1]heptane derivatives are extremely v

6 vi Preface useful synthons, few syntheses of natural products and bioactive compounds, using these synthons, have been described. In chapter Synthesis of 5,6- and 6,6-Spirocyclic Compounds, M. A. Brimble and L. A. Stubbing describe a number of recently reported and useful methods to synthesize 5,6- and 6,6-spirocyclic compounds, including their applications to the synthesis of natural products and bioactive compounds containing spiroacetal scaffolds. One can find dehydrative spirocyclization of dihydroxyketones, metal-catalyzed addition/elimination of allylic alcohols, acid-catalyzed spirocyclization of hemiacetals, spirocyclization of exo- and endocyclic enol ethers, transition-metalcatalyzed hydroalkoxylation of alkynes, electrophilic cyclization and oxa-michael cyclization, intramolecular hetero-michael addition, ring-opening of epoxides and cyclopropanes, cycloadditions, furan oxidation, intramolecular hydrogen abstraction, reductive cyclizations, ring-closing metathesis, and rearrangements. In chapter Synthesis of Seven-Membered-Ring Ethers and Lactones, O. Piva describes the access to saturated oxygenated 7-membered cyclic ethers, by ring expansion of oxygenated structures, by formation of C O and C C bonds using different methods. For 7-membered cyclic lactones, oxidative processes, halolactonization, lactonization of ω-hydroxyacids, tandem Suzuki coupling and lactonization, and ring enlargement are reported. For the synthesis of 8- to 10-membered ring ethers, in chapter Synthesis of Eight- to Ten-Membered-Ring Ethers, J. M. Contelles and E. Soriano focus on the formation of carbon carbon double bonds by metathesis, as well as on the formation of carbon carbon single bonds. The authors also report on the cyclization to form C O bonds, ring expansion, ring-opening, and rearrangement. Chapter Synthesis of 12- to 16-Membered-Ring Lactones is dedicated to the synthesis of 12- to 16-membered ring lactones. In this chapter, M. Kalesse and M. Cordes present an overview of the macrocyclization of seco-acids as well as new effective procedures to access 12- to 16-membered ring lactones such as ringclosing metatheses of alkynes and olefins. The authors also report the use of ketene sources and benzodioxinones to produce macrocyclic lactones. Nitrile oxide-olefin cycloaddition, intramolecular C H oxidative macrolactonization, and Yamaguchi and Mukaiyama macrocyclization as well as macrolactonization via thioester or using phosphorus reagents are described. I would like to express my sincere gratitude to all the authors of these chapters for their efforts and outstanding contributions. I would also like to thank B. Maes for giving me the opportunity to edit these two volumes, to Elizabeth Hawkins and Tanja Jaeger from Springer for coordinating the project, and to Fairin Miriam John Bennet for the editing process, for her help and patience. Finally, I hope that this book will be a good source of inspiration for those planning the synthesis of saturated oxygenated heterocycles, for solving specific synthetic problems, or for elaborating on new synthetic tools. Paris, France Janine Cossy

7 Contents for Volume I Synthesis of Substituted Tetrahydrofurans... 1 Jon D. Rainier Synthesis of Saturated Tetrahydropyrans Matthew A. Perry, Scott D. Rychnovsky, and Nicholas Sizemore Synthesis of Saturated Six-Membered Ring Lactones Kalanidhi Palanichamy and Krishna P. Kaliappan Synthesis of 7-Oxabicyclo[2.2.1]heptane and Derivatives Antonio J. Moreno-Vargas and Pierre Vogel Synthesis of 5,6- and 6,6-Spirocyclic Compounds Margaret A. Brimble and Louise A. Stubbing Index vii

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9 Contents for Volume II Synthesis of Seven-Membered Ring Ethers and Lactones Olivier Piva Synthesis of Eight- to Ten-Membered Ring Ethers Elena Soriano and José Marco-Contelles Synthesis of 12- to 16-Membered-Ring Lactones Martin Cordes and Markus Kalesse Index ix