ISSN 0265-0568 NPRRDF 6 1-1-1-60 (1 989) Natural Product Reports A journal of current developments in bio -organic chemistry Volume 6 Indexes CONTENTS ... 111 Preliminary pages for Volume 6 1-1 Index of Authors Cited 1-43 Subject Index ISSN 0265-0568 Coden NPRRDF Natural Product Reports A journal of current developments in bio -organic chemistry Volume 6 1989 The Royal Society of Chemistry Cambridge Natural Product Reports (ISSN 0265-0568) @ The Royal Society of Chemistry 1990 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.Printed in Great Britain by the University Press Cambridge ISSN 0265-0568 NPRRDF 6 1-645 1-1-1-60 (1 989) Natural Product Reports A journal of current developments in bio -organic chemistry Volume 6 CONTENTS 1 Recent Progress in the Chemistry of Indole Alkaloids and Mould Metabolites J. E. Saxton Reviewing the literature published between July I984 and June I987 55 Erythrina and Related Alkaloids A. S. Chawla and A. H. Jackson Reviewing the literature published between July I985 and June I987 67 Pyrrole Pyrrolidine Piperidine Pyridine and Azepine Alkaloids Reviewing the literature published between July I984 and June I987 79 Amaryllidaceae Alkaloids M. F. Grundon Reviewing the literature published between July 1985 and June 1987 85 Recent Advances in Chemical Ecology J.B. Harborne A. R. Pinder Reviewing the literature published between July 1985 and December I987 111 The Use of NMR Spectroscopy in the Structure Determination of Natural Products Two-Dimensional Methods A. E Derome 143 Biosynthetic Studies on Marine Natural Products M. J. Garson Reviewing the literature published until April 1988 171 The Biosynthesis of Porphyrins Chlorophylls and Vitamin B, F. J. Leeper Reviewing the literature published during I984 and 1987 205 The Polyether and Macrolide Antiobiotics Biogenetic Analysis and Structural Correlations D. O’Hagan 22 1 Pyrrolizidine Alkaloids D. J. Robins Reviewing the literature published between July 1984 and June 1987 231 Fatty Acids and Glycerides M.S. F. Lie Ken Jie Reviewing the literature published during 1984 and 1987 263 The Biosynthesis of Shikimate Metabolites P. M. Dewick Reviewing the literature published during I987 29 1 Limonene A. F. Thomas and Y. Bessikre 311 Enzyme Inhibitors in Medicine C S J. Walpole and R. Wrigglesworth Selectively reviewing the literature to the end of 1987 347 Diterpenoids J. R. Hanson Reviewing the literature published during 1987 359 Carotenoids and Polyterpenoids G. Britton Reviewing the literature published between January 1984 and December 1987 NATURAL PRODUCT REPORTS 1989 CONTENTS 393 Steroids Physical Methods D. N. Kirk Reviewing the literature mainly between mid 1985 and the end of 1987 405 P-Phenylethylamines and the Isoquinoline Alkaloids K.W. Bentley Reviewing the literature published between July 1987 and June 1988 433 Recent Progress in the Chemistry of Indole Alkaloids and Mould Metabolites J. E. Saxton Reviewing the literature published between July 1987 and June 1988 475 Triterpenoids J. D. Connolly and R. A. Hill Reviewing the literature published between July 1985 and December 1987 503 Muscarine Oxazole and Peptide Alkaloids and Other Miscellaneous Alkaloids J. R. Lewis Reviewing the literature published between July 1986 and June 1987 515 Pyrrolidine Piperidine and Pyridine Alkaloids A. R. Pinder Reviewing the literature published between July 1987 and June 1988 523 Indolizidine and Quinolizidine Alkaloids (The late) M. F. Grundon Reviewing the literature published between July 1985 and June 1987 537 Obituary Michael F.Grundon 1926-89 539 Steroids Reactions and Partial Syntheses A. B. Turner Reviewing the literature published between November 1986 and October 1987 577 Pyrrolizidine Alkaloids D. J. Robins Reviewing the literature published between July 1987 and June 1988 591 Coumarins R. D. H. Murray Reviewing the literature published between mid-1980 and mid-1988 625 Recent Advances in the Use of Enzyme-catalysed Reactions in Organic Synthesis N. J. Turner Reviewing the literature published between January 1986 and June 1988 645 Book Review The Dictionary of the Alkaloids ed. I. Southon and J. Buckingham Reviewed by R. B. Herbert vi Natural Product Reports EditoriaI Board Professor G.Pattenden (Chairman) University of Nottingham Dr D. V. Banthorpe University College London Dr J. R. Hanson University of Sussex Dr R. B. Herbert University of Leeds Professor M. I. Page The Polytechnic Huddersfield Professor T. J. Simpson University of Bristol ~ ~~ Natural Product Reports is a journal of critical reviews published bimonthly which is intended to foster progress in the study of natural products by providing reviews of the literature that has been published during well-defined periods on the topics of the general chemistry and biosynthesis of alkaloids terpenoids steroids fatty acids and 0-heterocyclic aliphatic aromatic and alicyclic natural products. Occasional reviews provide details of techniques for separation and spectroscopic identification and describe methodologies that are useful to all chemists and biologists who are actively engaged in the study of natural products.Articles in Natural Product Reports are commissioned by members of the Editorial Board or accepted by the Chairman for consideration at meetings of the Board. This journal includes reviews of books relating to natural products. Volumes for review should be sent to the editorial office for which the address is The Royal Society of Chemistry Thomas Graham House Science Park Milton Road Cambridge CB4 4WF and marked for the attention of the Senior Editor Reviews. Contributors to Volume 6 Bentley K. W. 405 Bessiere Y. 291 Britton G. 359 Harborne J. B. 85 Herbert R. B. 645 Hill R. A. 475 O’Hagan D.205 Pinder A. R. 67 515 Robins D. J. 221 577 Chawla A. S. 55 Connolly J. D. 475 Derome A. E. 111 Dewick P. M. 263 Garson M. J. 143 Grundon M. F. 79 523 Hanson J. R. 347 Jackson A. H. 55 Kirk D. N. 393 Leeper F. J. 171 Lewis J. R. 503 Lie Ken Jie M. S. F. 231 Murray R. D. H. 591 Saxton J. E. 1 433 Thomas A. F. 291 Turner A. B. 539 Turner N. J. 625 Walpole C. J. S. 311 Wrigglesworth R. 31 1 vii Nomenclature It is the policy of The Royal Society of Chemistry to en- courage the use of IUPAC and IUB Recommendations on nomenclature. Although many of the appropriate nomen-clature documents will be included in the new edition of the IUB publication ‘Biochemical Nomenclature and Related Documents ’ (published by The Biochemical Society London 1989) a selection of recent Recommendations that will be of particular interest to those who investigate the chemistry occurrence or biosynthesis of natural products includes Nomenclature of tetrapyrroles (Recommendations 1986) Pure Appl.Chem. 1987 59 779-832. Nomenclature and symbols for folic acid and related compounds (Recommendations 1986) Pure Appl. Chem. 1987 59 833-836; Eur. J. Biochem. 1987 168 251-253. Nomenclature of prenols (Recommendations 1986) Pure Appl. Chem. 1987 59 683-689; Eur. J. Biochem. 1987 167 181-184. Extension of Rules A- 1.1 and A-2.5 concerning numerical terms used in organic nomenclature (Recommendations 1986) Pure Appl. Chem. 1986 58 1693-1696. [The original versions of these Rules are in ‘Nomenclature of Organic Chemistry Sections A B C D E F and H’ 1979 Edition] Nomenclature of glycoproteins glycopeptides and peptidoglycans (Recommendations 1985) Eur.J. Biochem. 1986 159 1-6. ‘Enzyme Nomenclature (Recommendations 1984)’ Supplement 1 Corrections and additions Eur. J. Biochem. 1986 157 1-26. Recommendations for the presentation of thermodynamic and related data in biology (1985) Eur. J. Biochem. 1985 153 429434. Nomenclature for incompletely specified bases in nucleic acid sequences (Recommendations 1984) Eur. J. Biochem. 1985 150 1-5 (see also Eur. J. Biochem. 1986 157 1). ‘Enzyme Nomeclature 1984’ (Recommendations of the Nomenclature Committee of the International Union of Biochemistry on the nomenclature and classification of enzyme- catalysed reactions) Academic Press Orlando Florida 1984.Nomenclature and symbolism for amino acids and peptides (Recommendations 1983) Pure Appl. Chem. 1984 56 595424; Eur. J. Biochem. 1984 138 9-37 (see also Eur. J. Biochem. 1985 152 1 and the Newsletter 1985 of NC-IUB and JCBN ibid. 1985 146 pp. 238 and 239 and the Newsletter 1986 ibid. 1986 154 pp. 485 and 486). Abbreviations and symbols for the description of conformations of polynucleotide chains (Recommendations 1982) Pure Appl. Chem. 1983 55 1273-1280; Eur. J. Biochem. 1983 131 9-15 (see also the Newsletter 1984 of NC-IUB and JCBN Eur. J. Biochem. 1984 138 p. 7). Symbols for specifying the conformation of polysaccharide chains (Recommendations 198 l) Pure Appl. Chem. 1983 55 1269-1272; Eur.J. Biochem. 1983 131 5-7. Nomenclature of retinoids (Recommendations 198I) Pure Appl. Chem. 1983 55 721-726; Eur. J. Biochem. 1982 129 1-5. Symbolism and terminology in enzyme kinetics (Recommendations 1981) Eur. J. Biochem. 1982 128 281-291. Polysaccharide nomenclature (Recommendations 1980) Pure Appl. Chem. 1982 54 1523-1526; Eur. J. Biochem. 1982 126,439-441. Abbreviated terminology of oligosaccharide chains (Recommendations 1980) Pure Appl. Chem. 1982 54 1517-1522; Eur. J. Biochem. 1982 126,433437. Nomenclature of vitamin D (Recommendations 198I) Pure Appl. Chem. 1982 54 151 1-1516; Eur. J. Biochem. 1982 124 223-227. Nomenclature of tocopherols and related compounds (Recommendations 1981) Pure Appl. Chem. 1982 54 1507-1510; Eur.J. Biochem. 1982 123 473475. The most recent of the lists of restriction endonucleases and their isoschizomers (compiled by R. J. Roberts) was in Nucleic Acids Res. 1988 16 R271-R313 its predecessors being ibid. 1987 15 R189-R217 ibid. 1985 13 r165-r200 and ibid. 1983 11 r135-rl67. Recent codes of nomenclature for organisms include ‘International Code of Nomenclature of Bacteria and Statutes of the International Committee on Systematic Bacteriology (1976) Revision)’ ed. S. P. Lapage P. H. A. Sneath E. F. Lessel V. B. D. Skerman H. P. R. Seeliger and W. A. Clark American Society for Microbiology Washington D.C. U.S.A. 1976. [Appendix 2 of this publication (Approved Lists of Bacterial Names) appeared in Znt. J. Syst. Bacteriol. 1980 30 225420.1 ‘International Code of Botanical Nomenclature (1987)’ ed.W. Greuter H. M. Burdett W. G.Chaloner V. Demoulin R. Grolle D. L. Hawksworth D. H. Nicholson P. C. Silva F. A. Stafleu E. G. Voss and J. McNeill Koeltz Scientific Books Konigstein Federal Republic of Germany 1988. ‘International Code of Zoological Nomenclature ’ 3rd edn. ed. W. D. L. Ride C. W. Sabrosky G. Bernardi R. V. Melville J. 0. Corliss J. Forest K. H. L. Key and C. W. Wright International Trust for Zoological Nomenclature in association with the British Museum (Natural History) London U.K. and the California Press Berkeley and Los Angeles U.S.A. 1985. viii