General And Synthetic Methods., Volume 3

General and Synthetic Methods Volume 3 A Specialist Periodical Report General and Synthetic Methods Volume 3 A Review of the Literature Pub ished during 1978 Senior Reporter G. Pattenden, Department of Chemistry, University of Nottingham Reporters K. Cooper, University of Nottingham A. B. Holmes, University of Cambridge D. C. Howell, Lilly Research Centre, Windlesham, Surrey M. G. Hutchings, I.C.I. Organics, Manchester R. C. F. Jones, University of Nottingham G. Kneen, Wellcome Research Laboratories, Beckenham, Kent D. W. Knight, University College, Cardiff M. Mellor, Bush Boake Allen Ltd., London S. M. Roberts, University of Salford W. J. Ross, Lilly Research Centre, Windlesham, Surrey D. J. Thompson, /.C./. Organics, Manchester S. Turner, Polytechnic of North London The Chemical Society Burlington House, London, W I V OBN British Library Cataloguing in Publication Data General and synthetic methods.(Chemical Society. Specialist periodical reports). VOl. 3 1. Chemistry, Organic-Synthesis I. Pattenden, Gerald 11. Series 547l.2 QD262 ISBN 0-85186-730-8 ISSN 0141-2140 Copyright @ 1980 The Chemical Society All Rights Reserved No part of this book may be reproduced or transmitted in any form or by any means -graphic, electronic, including photocopying, recording, taping or information storage and retrieval systems - without written permission from The Chemical Society Set in Times on Linotron and printed offset by J. W. Arrowsmith Ltd., Bristol, England Made in Great Britain In trod ucti0n This report on General and Synthetic Methods is similar in scope and format to the previous two volumes in the series. Developments in the synthesis of saturated heterocycles, unfortunately omitted from Volume 2, are covered in this volume (Chapter 8), and a special report on ‘Photochemistry in Synthesis’ (Chapter 10) is included. There have been several high points in synthesis during 1978, but perhaps one should use this opportunity to single out the achievements of one chemist, the illustrious E. J. Corey, who during 1978 reported first total syntheses of gibberellic acid, the plant growth regulator (Chapter 7, ref. l),erythronolide B, the aglycone of the erythromycin B family of antibiotics (Chapter 9, ref. 17)’ and of N-methylmaysenine, one of the antitumoural maytensenoids (Chapter 9, ref. 23), each a major achievement in synthesis design and execution. July 1979 G. PATTENDEN Contents Chapter 1 Saturated and Unsaturated Acyclic Hydrocarbons By D. C. Horwell 1 1 Introduction 1 2 Saturated Hydrocarbons 2 3 Olefinic Hydrocarbons 4 4 Conjugated 1,3-Dienes 19 5 1,4-, 1 , 5 , and 1,6-Dienes 24 6 Allenic Hydrocarbons 27 7 Acetylenic Hydrocarbons 29 8 Enynes and Polyunsaturated Hydrocarbons 32 Chapter 2 Aldehydes and Ketones B y .S. M. Roberts 36 1 Preparations of Aldehydes and Ketones By Oxidation of Alcohols Thio- and Seleno-ketones Cyclic Ketones Dicarbonyl Compounds Other Preparations 36 36 37 37 39 41 2 Reactions of Aldehydes and Ketones Alkylation Aldol Reactions Reduction General Reactions 46 46 48 49 50 3 Preparations of Unsaturated Aldehydes and Ketones 54 4 Reactions of Unsaturated Aldehydes and Ketones Alkylation 60 60 vii ... General and Synthetic Methods Vlll Reduction Conjugate Addition General Reactions 61 62 65 5 Protected Aldehydes and Ketones Preparation Regeneration of Aldehydes and Ketones Reactions 66 66 67 68 6 Halogeno-derivatives Preparation Reactions 71 71 72 7 Acyl, Homoen