13C-NMR of Natural Products, Volume 2: Diterpenes PDF
Preview 13C-NMR of Natural Products, Volume 2: Diterpenes
13C-NMR of Natural Products Volume 2 Diterpenes 13C-NMR of Natural Products Volume 2 Diterpenes Atta-ur-Rahman and Viqar Uddin Ahmad H.E.J. Research Institute of Chemistry University of Karachi Karachi, Pakistan Springer Science+Business Media, LLC Llbrary of Congress Cataloglng-ln-Publlcatlon Data 13C-NMR of natural products / Atta-ur-Rahman and Viqar Uddin Ahmad. p. cm. Includes bibliographical references and index. Contents: v. 1. Monoterpenes and sesquiterpenes v. 2. Dlterpenes. ISBN 978-1-4613-6446-7 ISBN 978-1-4615-3288-0 (eBook) DOI 10.1007/978-1-4615-3288-0 1. Nafural products--Analysis. 2. Nuclear magnetiC resonance spectroscopy. 1. Rahman. Atta-ur-, 1942- II. Ahmad, Viqar Uddin. III. Title: Carbon-thirteen NMR of natural products. OD415.A267 1991 547.3·0877--dc20 91-10877 CIP ISBN 978-1-4613-6446-7 © 1992 Springer Science+Business Media New York Originally published by Plenum Press, New York in 1992 AlI rights reserved No part of this book may be reproduced, stored in a retrievai system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permis sion from the Publisher PREFACE Natural product chemistry presents a vast and exciting area which has attracted the attention of some of the foremost organic chemists. With the development of modem spectroscopic techniques, the number of new natural products continues to grow exponentially thereby placing at the hands of phytochemists and pharmacologists a vast array of novel and interesting compounds with potential for drug development. The need for books which present spectral data of such compounds has accordingly grown. The present volume, which is the second of this new series, covers the J3C-NMR data of diterpenes reported till late 1989. The compounds are arranged according to their structural types in various subclasses. Within each subclass, they are arranged in order of increasing molecular weight Compounds in the same subclass and having the same molecular weight are arranged in order to increasing carbon number while those having the same molecular formula are arranged alphabetically. In case the J3C-chemical shifts were not assigned by the authors, then these are presented unassigned below the structures. If the chemical shifts have been reported in several solvents, then the values presented are those in CDC13, but references have been included to their data in other solvents. We have avoided giving long chemical names of compounds and used trivial names but where trivial names were not given by the authors, then the compounds have been designated by alphabets (representing the first alphabets of the plant genus and species) followed by a number. The data given is for natural compounds and the data for simple derivatives has only been given where the data of the parent natural compounds was not available. The symbols *,**, ***, +, ++, +++, #, @, $, ct., &, have been employed to indicate interchangeability of assigned values. The numbering systems used are given at the beginning of each subclass. Compound name, molecular formula, molecular weight, source and compounds-type indices have been included, which should add to the utility of the book. The authors wish to thank the following research fellows for their help in the literature survey: Miss Anis Fatima, Miss Jahan Ara, Miss Nazli Rasool, Miss Rehana Perveen, Miss Rubeena Saleem, Miss Saleha Ishrat, Miss Seema Iqbal, Miss Shahida Begum and Miss Zahida Begum. We are grateful to Mr. Kamran Faisal Khan, Mr. Mohammad Afzal Butt, Mr. Wajih-ul-Hasnain, Mr, Mohammad Shakir and Mr. Asif Mehmood Raja for typing of the manuscript. Our thanks go to Mr. Mehmood Alam for the secretarial work and to Mr. Abdul Hafeez for drawing the structures. We are indebted to Zelin Private Limited (Karachi), Pakistan Atomic Energy Commission (Islamabad), Sumitomo Corporation (Tokyo) and Rotary Club (Karachi) for financial support. Finally we wish to express our sincere gratitude to Prof. K. Antonakis, Prof. F. Arcamone, Prof. Y. Asakawa, Dr. Fatima Z. Basha, Prof. Jan Bergman, Prof. H.1. Bestmann, Prof. H. Budzikiewicz, Prof. L. Castedo, Prof. M. Chierichetti, Prof. J.D. Connolly, Prof. B. Danieli, Prof. S. Dev, Prof. H. Duddeck, Mr. E.B. Gapit, Prof. B.Q. Guevara, Prof. T. Higa, Dr. H. Hirota, Miss J. Hudson, Dr. Byung-Hoon Han, Prof. S. Ito, Prof. P. Joseph-Nathan, Prof. J. Jurczak, Dr. L. Kenne, Prof. S.V. Kessar, Prof. W. Kraus, Prof. J.P. Kutney, Dr. J. McLeod, Prof. P.w. Le Quesne, Prof. J. Levy, Mr. K. Mahmood, Dr. S. Malik, Prof. K. Mori, Dr. T. Nakano, Prof. Nanjun-Sun, Prof. I. Ninomiya, Prof. M. Nishizawa, Prof. C. Oehlschlager, Prof. K.A. Parker, Dr. A. Panthong, Prof. J.H. Pazur, Prof. G.D. Prestwich, Prof. A.V. Rama Rao, Prof. V. Reutrakul, Prof. M.Y. Sargent, Prof. P. Sinay, Prof. Y. Shizuri, Prof. G. Snatzke, Prof. W. Steglich, Prof. c. Szantay, Dr. F. Tillequin, Prof. A. Vasella, Prof. R. Verpoorte, Prof. R. Vlahov, Prof. W. Voelter, Prof. D. Walton, Prof. Z.J. Witczak. Prof. Xu.xing-Xiang, Prof. X.x. Xu, Prof. Yong-Long Liu, Prof. A. Zamojski and Prof. K.P. Zeller for supply of copies of various publications. Atta-ur-Rahman Ph.D. (Cantab.), Sc.D. (Cantab). Viqar Uddin Ahmad Ph.D. (Kar.), Dr.rer.nat. (Bonn) v CONTENTS Diterpenes Linear ............................................................................. 3 Difuran Terpenoid .................................................................... 23 Oxepane ................................. , .... " .......... , ........................ 26 Bisabolane Isoprenologue ............................................................... 28 Retinane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 30 Labdane ........................................................................... 33 Seco-Labdane ...................................................................... 136 Chettaphanane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 139 Seco-Chettaphanane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 144 Clerodane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 146 Pimarane ......................................................................... 248 Abietane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 286 Seco-Abietane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 318 Abeo-Abietane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 320 Totarane 324 Kaurane 325 Seco-Kaurane ...................................................................... 380 Beyrane .......................................................................... 383 Seco-Beyrane ...................................................................... 391 Cassane .......................................................................... 392 Seco-Cassane ...................................................................... 394 Cleistanthane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 395 Seco-Cleistanthane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . " 399 Rosane .................................................................... '" .. " 400 Lanugon . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 407 Coleon ........................................................................... 410 VII Spongian .................................•....................................... 412 Seco-Spongian . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 430 Gibbane .......................................................................... 435 Trachylobane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 436 Atisane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 438 Cembrane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 446 Seco-Cembrane ..................................................................... 479 Iso-Cembrane ...................................................................... 480 Casbane .......................................................................... 482 Berdimerane 484 Dollabellane 486 Dolastane ......................................................................... 504 Grindelane ........................................................................ 511 Ericacane ......................................................................... 513 Fusicoccin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 514 Seco-Fusicoccin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 516 Ja trophane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 517 Xeniaphyllane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 519 Xenicin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 525 Guiane Isoprenologue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 535 Portulal . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 541 Undecane 544 Daphnane 547 Tigliane 549 •••••••••••••••••••• Ii ••••••••••••••••••••••••••••••••••••••••••••••••••••• Briarane 552 Cladiellane ........................................................................ 566 Asbestinin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 572 Cubitane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 575 VIII Cyclonane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 578 Biflorane ......................................................................... 584 Germacrane Isoprenologue ............................................................. 594 Sacculatane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 598 Irieol ............................................................................ 599 Spatane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 603 Ginkgolide ........................................................................ 605 Crotofolane . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 608 Stemodane ........................................................................ 609 Enmein ........................................................................... 611 Verrucosane 614 Barbacenane 615 Trinerverane 617 Viscidane ......................................................................... 619 Miscellaneous Diterpenes 622 Indexes Name Index ....................................................................... 681 Source Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 699 Compound Type Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 725 Molecular Formula Index .............................................................. 745 Molecular Weight Index ............................................................... 775 IX DITERPENES LINEAR Basic skeleton: 20 16 111111111111!llllllllllllllllllllllllllllllllil!111111IIIIIIIIIIIIIIIII!IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII!IIIIIIII B-SPRINGENE Source: Antidorcas marsupiaZis Mol. formula: C20H32 Mol. wt.: 272 Solvent: CDCl3 17.7 16.0 16.0 B.V. Burger, M. Le Roux. H.S.C. Spies. V. Truter and R.C. Bigalke. Tetrahedron Lett., (52), 5221 (1978). 3 (5~. 9~)-13.14-EPOXY-6.10.14-TRIMETHYLPENT ADECA-5. 9-DIEN-2-0NE Source: Cystophol'a monilifo1'l11is Mol. formula: C18H3002 Mol. wt.: 278 Solvent: CDCl3 o CH : 15.8, 15.8, 18.6, 27.3 and 29.8 3 CH2: 22.3, 24.8, 26.3, 36.2, 39.5 and 43.6 CH: 64.1, 122.7 and 124.7 C: 58.2, 134.2 and 136.3 C=O: 208.8 • LA. van Altena, Aust. J. Chern., 41 (1), 49 (1988). 1I1111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111111III (2E,6E.10E.13E)-3, 7, 1l,15-TETRAMETHYL-HEXADECA-2,6, 10, - - - - 13,15-PENTENOL Source: Biful'caria biful'cata Mol. formula: C20H 320 Mol. wt.: 288 Solvent: CDCl3 42.7 125.1 39.4 123.8 39.4 123.4 18.5 OH 114.3 15.9 15.8 16.1 L. Semmak, A. Zerzouf, R. Valls, B. Banaigs, G. Jeanty and C. Francisco, Phyto chemistry, 27(7), 2347 (1988). 4
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