ISSN 1350-4894 COGSE6 3 1-1-1-54 (1996) ~~~~~~ ~ ~ Contemporary Organic Synthesis A journal of current developments in Organic Synthesis V O L U M E 3 INDEXES CONTENTS ... 111 Contents of volume 3 iv Contributors to volume 3 V Journal details 1-1 Index of authors cited 1-29 Subject index Notice to librarians: Journal binding Preliminary pages iii-vi are designed to be bound at the beginning of volume 3, and the Indexes bound at the end, 1ISSN 1350-4894 COGSE6 3 1-1-1-54 (1996) ~~~~~~ ~ ~ Contemporary Organic Synthesis A journal of current developments in Organic Synthesis V O L U M E 3 INDEXES CONTENTS ... 111 Contents of volume 3 iv Contributors to volume 3 V Journal details 1-1 Index of authors cited 1-29 Subject index Notice to librarians: Journal binding Preliminary pages iii-vi are designed to be bound at the beginning of volume 3, and the Indexes bound at the end, 1ISSN 1350-4894 COGSE6 3 1-568, 1-1-1-54 (1996) Contemporary Organic Synthesis A journal of current developments in Organic Synthesis V O L U M E 3 CONTENTS 1 19 41 65 93 125 133 151 173 201 229 243 259 277 295 Stoichiometric applications of organotransition metal complexes in organic synthesis Timothy J.Donohoe Reviewing the literature published between 1 September 1994 and 30 April 1995 Saturated and partially unsaturated carbocycles Gerald Pattenden Reviewing the literature published between January 1994 and April 1995 The enediyne and dienediyne based antitumour antibiotics. Methodology and strategies for total synthesis and construction of bioactive analogues.Part 1 Hem6 Lhermitte and David S. Grierson Reviewing the literature published up to 15 October 1995 Alcohols, ethers and phenols C. S. Hau, Ashley N. Jarvis and Joseph B. Sweeney Reviewing the literature published between August 1993 and February I994 The enediyne and dienediyne based antitumour antibiotics. Methodology and strategies for total synthesis and construction of bioactive analogues. Part 2 Hem6 Lhermitte and David S. Grierson Reviewing the literature published up to 15 November I995 The discovery of fluconazole Reviewing the literature published up to December 1994 Organic halides Stephen I? Marsden Reviewing the literature published between 1 July 1993 and 30 June 1995 Aldehydes and ketones Patrick G. Steel Reviewing the literature published between October 1994 and September I993 Recent developments in chemical oligosaccharide synthesis Geert- Jan Boons Reviewing the literature published up to October 1995 Main group organometallics in synthesis Martin Wills Reviewing the literature published between January 1994 and June I995 Saturated oxygen heterocycles Reviewing the literature published between October 1994 and September I995 Carboxylic acids and esters Tammy Ladduwahetty Reviewing the literature published between 1 August 1994 and 31 July 1995 Saturated nitrogen heterocycles Timothy Harrison Reviewing the literature published in 1995 Catalytic applications of transition metals in organic synthesis Graham J.Dawson, Justin F. Bower and Jonathan M. J. Williams Reviewing the literature published between I September 1994 and 31 October 1995 Saturated and unsaturated lactones Ian Collins Reviewing the literature published between 1 August 1994 and 31 October 1995 Christopher D.J. Boden and Ken Richardson Christopher J. Burns and Donald S. Middleton ... 111323 345 373 397 433 447 473 499 535 I- 1 1-29 Amines and amides Michael North Reviewing the literature published in 1995 Synthetic approaches to rapamycin Mark C. Norley Reviewing the literature published up to August I995 Synthetic applications of flash vacuum pyrolysis Hamish McNab Reviewing the literature published between 1990 and 1995 Protecting groups Krzysztof Jarowicki and Philip Kocienski Reviewing the literature published in 1995 The synthesis of quinones Peter T. Gallagher Reviewing the literature published between 1 January 1991 and 31 December 1995 The intramolecular Heck reaction Richard J.Middleton Reviewing the literature published up to the end of 1995 Saturated and partially unsaturated carbocycles Kevin I. Booker-Milburn and Andrew Sharpe Reviewing the literature published between May 1995 and April 1996 Synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones Christopher M. Rayner Reviewing the literature published between March 1995 and May 1996 The synthesis of carbocyclic aromatic systems Andrew C. Williams Reviewing the literature published between Janualy 1992 and December 1995 Susan E. Gibson (nee Thomas) and Index of authors cited Subject index Contributors to Volume 3 Boden, Christopher D.J., 19 Booker-Milburn, Kevin I., 473 Boons, Geert-Jan, 173 Bower, Justin F., 277 Burns, Christopher J., 229 Collins, Ian, 295 Dawson, Graham J., 277 Donohoe, Timothy J., 1 Gallagher, Peter T., 433 Gibson (nee Thomas), Susan E., 447 Grierson, David S., 41, 93 Harrison, Timothy, 259 Hau, C. S., 65 Jarowicki, Krzysztof, 397 Jarvis, Ashley N., 65 Kocienski, Philip, 397 Ladduwahetty, Tammy, 243 Lhermitte, Heme, 41, 93 Marsden, Stephen P., 133 McNab, Hamish, 373 Middleton, Donald S., 229 Middleton, Richard J., 447 Norley, Mark C., 345 North, Michael C., 323 Pattenden, Gerald, 19 Rayner, Christopher M., 499 Richardson, Ken, 125 Sharpe, Andrew, 473 Steel, Patrick G., 151 Sweeney, Joseph B., 65 Williams, Jonathan M. J., 277 Williams, Andrew C., 535 Wills, Martin, 201 iv~~ Contemporary Organic Synthesis Editorial Board Professor G.Pattenden, FRS (Chairman), University of Nottingham Professor P. D. Bailey, Heriot- Watt University Dr S. E. Gibson (nee Thomas), Imperial College of Science, Technology, and Medicine Professor P. J. Kocienski, University of Southampton Professor C. J. Moody, Loughborough University of Technology Professor E. J. Thomas, University of Manchester International Advisory Board Professor E. J. Corey, Harvard University Professor S. Hanessian, Universite' de Montrial Professor M. Julia, Universite' de Paris XI (Paris-Sud) Professor P. D. Magnus, University of Texas at Austin Professor G. Mehta, University of Hyderabad Professor K. C. Nicolaou, The Scripps Research Institute and University of Professor R.Noyori, Nagoya University Professor L. E. Overman, University of California, Irvine Professor L. F. Tietze, University of Gottingen California at Sun Diego, La Jolla Contemporary Organic Synthesis is a bimonthly journal which aims to review and provide perspective in all aspects of methodology, selectivity and efficiency in contemporary synthesis. As well as covering all the principles and methods in functional group chemistry and interconversions, organometallic chemistry and asymmetric synthesis will feature prominently; so too will modern aspects of strategy and computer aided design, biotransformations and protecting group protocols. Special methods and techniques, such as sonochemistry, FVP, electroorganic synthesis and supported catalysis will be included as occasional articles, and the manner in which synthesis addresses problems and provides solutions in biology, medicine, agriculture, the environment and new materials, will also be encompassed. Contemporary Organic Synthesis aims to be proactive, drawing attention to new opportunities and new directions, providing timely information to the synthetic chemist who needs to keep abreast of developments in the field.Although the majority of articles are intended to be specially commissioned, the Society is always prepared to consider offers of articles for publication. In such cases a short synopsis, rather than the completed article, should be submitted to Dr S. R. Buxton, Managing Editor, Organic Publications, The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge CB4 4WF, UK. Members of The Royal Society of Chemistry may subscribe to Contemporary Organic Synthesis by placing their orders on the Annual Subscription renewal forms in the usual way.All other orders accompanied with payment should be sent directly to The Royal Society of Chemistry, The Distribution Centre, Blackhorse Road, Letchworth, Herts SG6 lHN, England. 1996 subscription rates: EEA f185, USA $350, Canada 2190 (plus GST), Rest of the World X190. Contemporary Organic Synthesis is published 6 times a year in February, April, June, August, October and December. Airfreight and mailing in the USA by Mercury Airfreight International Ltd, 2323 Randolph Avenue, Avenel, New Jersey, NJ 07001, USA and at additional mailing offices.Second class postage is paid at Rahway, NJ. USA Postmaster: Send address changes to Contemporary Organic Synthesis, c/o Mercury Airfreight International Ltd, 2323 Randolph Avenue, Avenel, New Jersey 07001. All other dispatches outside the UK are by Bulk Airmail within Europe and Accelerated Surface Post outside Europe. (3 The Royal Society of chemistry, 1997 All rights reserved No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form, or by any means, electronic, mechanical, photographic, recording or otherwise, without the prior permission of the publishers. Typeset in Great Britain by Unicus Graphics Ltd Printed in Great Britain by Whitstable Litho Ltd V~~ Contemporary Organic Synthesis Editorial Board Professor G.Pattenden, FRS (Chairman), University of Nottingham Professor P. D. Bailey, Heriot- Watt University Dr S. E. Gibson (nee Thomas), Imperial College of Science, Technology, and Medicine Professor P. J. Kocienski, University of Southampton Professor C. J. Moody, Loughborough University of Technology Professor E. J. Thomas, University of Manchester International Advisory Board Professor E. J. Corey, Harvard University Professor S. Hanessian, Universite' de Montrial Professor M. Julia, Universite' de Paris XI (Paris-Sud) Professor P. D. Magnus, University of Texas at Austin Professor G. Mehta, University of Hyderabad Professor K. C. Nicolaou, The Scripps Research Institute and University of Professor R. Noyori, Nagoya University Professor L. E.Overman, University of California, Irvine Professor L. F. Tietze, University of Gottingen California at Sun Diego, La Jolla Contemporary Organic Synthesis is a bimonthly journal which aims to review and provide perspective in all aspects of methodology, selectivity and efficiency in contemporary synthesis. As well as covering all the principles and methods in functional group chemistry and interconversions, organometallic chemistry and asymmetric synthesis will feature prominently; so too will modern aspects of strategy and computer aided design, biotransformations and protecting group protocols. Special methods and techniques, such as sonochemistry, FVP, electroorganic synthesis and supported catalysis will be included as occasional articles, and the manner in which synthesis addresses problems and provides solutions in biology, medicine, agriculture, the environment and new materials, will also be encompassed.Contemporary Organic Synthesis aims to be proactive, drawing attention to new opportunities and new directions, providing timely information to the synthetic chemist who needs to keep abreast of developments in the field. Although the majority of articles are intended to be specially commissioned, the Society is always prepared to consider offers of articles for publication. In such cases a short synopsis, rather than the completed article, should be submitted to Dr S. R. Buxton, Managing Editor, Organic Publications, The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge CB4 4WF, UK.Members of The Royal Society of Chemistry may subscribe to Contemporary Organic Synthesis by placing their orders on the Annual Subscription renewal forms in the usual way. All other orders accompanied with payment should be sent directly to The Royal Society of Chemistry, The Distribution Centre, Blackhorse Road, Letchworth, Herts SG6 lHN, England. 1996 subscription rates: EEA f185, USA $350, Canada 2190 (plus GST), Rest of the World X190. Contemporary Organic Synthesis is published 6 times a year in February, April, June, August, October and December. Airfreight and mailing in the USA by Mercury Airfreight International Ltd, 2323 Randolph Avenue, Avenel, New Jersey, NJ 07001, USA and at additional mailing offices. Second class postage is paid at Rahway, NJ. USA Postmaster: Send address changes to Contemporary Organic Synthesis, c/o Mercury Airfreight International Ltd, 2323 Randolph Avenue, Avenel, New Jersey 07001. All other dispatches outside the UK are by Bulk Airmail within Europe and Accelerated Surface Post outside Europe. (3 The Royal Society of chemistry, 1997 All rights reserved No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form, or by any means, electronic, mechanical, photographic, recording or otherwise, without the prior permission of the publishers. Typeset in Great Britain by Unicus Graphics Ltd Printed in Great Britain by Whitstable Litho Ltd V