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The first in a new series, this book provides chemists an effective, much-needed way to stay abreast of recent developments in organic synthesis. The 103 articles review the leading synthetic procedures developed from 2003 - 2005, discussing their significance and their applications. More than 100 reactions are covered, including Heterocycle Construction by Grubbs Metathesis, Enantioselective C-C Bond Construction, and Organic Reactions in Ionic Liquids.
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Organic Synthesis State of the Art 2003-2005 Organic Synthesis State of the Art 2003-2005 Organic Synthesis State of the Art 2003-2005 Douglass F. Taber University of Delaware Newark, DE A JOHN WILEY &SONS, INC., PUBLICATION Copyright 02006 by John Wiley & Sons, lnc. All rights reserved. Published by John Wiley & Sons, Inc., Hoboken, New Jersey. Published siinultaneously in Canada. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, lnc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 1 1 1 River Street, Hoboken, NJ 07030, (201) 748-601 I , fax (201) 748-6008, or online at http://www.wiley.com/go/permission. Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762-2974, outside the United States at (317) 572-3993 or fax (317) 572-4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic format. For information about Wiley products, visit our web site at www.wiley.com. Library of Congress Cataloging-in-Publication Data is available. ISBN-13 978-0-470-0533 1-7 ISBN-I0 0-470-0533 1-3 Printed in the United States of America 1 0 9 8 7 6 5 4 3 2 1 Contents ix Preface 1. Transition metal-mediated reactions in organic synthesis 2. Biotransformations in organic synthesis 3. Catalytic Enantioselective Synthesis 4. Enantioselective Synthesis of Borrelidin 5. Enantioselective Ring Construction 1 2 4 6 8 6. New Routes to Heterocycles 10 8. Total Synthesis of Ingenol 14 7. Total Synthesis of the Galbulimima Alkaloid GB 13 9. Best Synthetic Methods: Functional Group Transformations 10. New Methods for Carbon-Carbon Bond Formation 11. Mini-Review: Organic Reactions in Ionic Liquids 12. Adventures in Polycyclic Ring Construction