Skip to main content
SpringerLink
Log in

Some Applications of Nuclear Magnetic Resonance Spectroscopy in Natural Product Chemistry

  • Chapter
Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles

Abstract

In the last decade, the organic chemist’s approach to Natural Product Chemistry has undergone a considerable change. It is now apparent that the structures of the majority of natural products can be determined absolutely and in a surprisingly short time by the method of X-ray crystallography. This method is however expensive, and at present it is not feasible to determine the structures of many natural products, particularly simple ones, by this method. Even so, the organic chemist is now conscious that the expenditure of several years on the determination of a structure of a natural product is no longer justified. Fortunately recent developments in various spectroscopic methods now enable the organic chemist to solve structures much more efficiently than in the past.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Abraham, R. J., L.D. Hall, L. Hough and K. A. McLauchlan: A Proton Resonance Study of the Conformations of Carbohydrates in Solution. Part I. Derivatives of 1,2-O-Isopropylidene- α-D-xylohexofuranose. J. Chem. Soc. (London) 1962, 3699.

    Google Scholar 

  2. Abraham, R. J., K. A. McLauchlan, L. D. Hall and L. Hough: The Conformations of some Furanose Derivatives in Solution by Proton Magnetic Resonance. Chem. and Ind. 1962, 213.

    Google Scholar 

  3. Arthur, H. R. and W. D. Ollis: A Revised Structure for Avicennin. J. Chem. Soc. (London) 1963, 3910.

    Google Scholar 

  4. Ayer, W. A., C. E. McDonald and J. B. Stothers: The Stereochemistry of Maleopimaric Acid and the Long Range Shielding Effect of the Olefinic Bond. Canad. J. Chem. 41, 1113 (1963).

    CAS  Google Scholar 

  5. Balasubramanian, S. K., D. H. R. Barton and L. M. Jackman: Diterpenoid Bitter Principles. Part V. The Constitution of Palmarin and its Congeners. J. Chem. Soc. (London) 1962, 4816.

    Google Scholar 

  6. Banwell, C. N. and N. Sheppard: (H—H) Coupling Constants in the Nuclear Magnetic Resonance Spectra of Hydrocarbon Groupings. Discuss. Faraday Soc. No. 34, 115 (1962).

    Article  Google Scholar 

  7. Barber, M. S., J. B. Davis, L. M. Jackman and B. C. L. Weedon: Studies in Nuclear Magnetic Resonance. Part I. Methyl Groups of Carotenoids and Related Compounds. J. Chem. Soc. (London) 1960, 2870.

    Google Scholar 

  8. Barber, M. S., A. Hardisson, L. M. Jackman and B. C. L. Weedon: Studies in Nuclear Magnetic Resonance. Part IV. Stereochemistry of the Bixins. J. Chem. Soc. (London) 1961, 1625.

    Google Scholar 

  9. Barber, M. S., L. M. Jackman, C. K. Warren and B. C. L. Weedon: Carotenoids and Related Compounds. Part IX. The Structures of Capsanthin and Capsorubin. J. Chem. Soc. (London) 1961, 4019.

    Google Scholar 

  10. Barber, M.S., L. M. Jackman and B. C. L. Weedon: The Structures of Spirilloxanthin and Related Carotenoids. Proc. Chem. Soc. (London) 1959, 96.

    Google Scholar 

  11. Barton, D. H. R. and D. Elad: Colombo Root Bitter Principles. Part II. The Constitution of Columbin. J. Chem. Soc. (London) 1956, 2090.

    Google Scholar 

  12. Barton, D. H. R., K. H. Overton and A. Wylie: Diterpenoid Bitter Principles. Part IV. Investigations on the Constitution of Palmarin. J. Chem. Soc. (London) 1962, 4809.

    Google Scholar 

  13. Bates, R. B. and D. M. Gale: Stereochemistry of Trisubstituted Double Bonds in Terpenoids. J. Amer. Chem. Soc. 82, 5749 (1960).

    Article  CAS  Google Scholar 

  14. Batterham, T. J. and R. J. Highet: Nuclear Magnetic Resonance Spectra of Flavonoids. Austral. J. Chem. 17, 428 (1964).

    CAS  Google Scholar 

  15. Bhacca, N. S. and D.H.Williams: Applications of N. M. R. Spectroscopy in Organic Chemistry. Illustrations from the Steroid Field. San Francisco: Holden-Day, Inc. 1964.

    Google Scholar 

  16. Buchschacher, P., M. Cereghetti, H. Wehrli, K. Schaffner und O. Jeger: Über Steroide und Sexualhormone. 212. Mitt. Photochemische Umwandlungen von 20-Keto-pregnan-Verbindungen. Helv. Chim. Acta 42, 2122 (1959).

    Article  CAS  Google Scholar 

  17. Burrell, J. W. K., R. F. Garwood, L. M. Jackman, E. Oskay and B. C. L. Weedon: Carotenoids and Related Compounds. Part XIII. Stereochemistry and Synthesis of Geraniol, Nerol, Farnesol and Phytol. J. Chem. Soc. (London) (in press, 1965).

    Google Scholar 

  18. Burrell, J.W.K., L. M. Jackman and B. C. L. Weedon: Stereochemistry and Synthesis of Phytol, Geraniol and Nerol. Proc. Chem. Soc. (London) 1959, 263.

    Google Scholar 

  19. Burrows, B. F., W. D. Ollis and L. M. Jackman: Sericetin. Proc. Chem. Soc. (London) 1960, 177.

    Google Scholar 

  20. Chamberlain, N. F.: Determining Molecular Structure by Nuclear Magnetic Resonance of Hydrogen. Analyt. Chemistry 31, 56 (1959).

    Article  CAS  Google Scholar 

  21. Clark-Lewis, J. W., L. M. Jackman and T. M. Spotswood: Nuclear Magnetic Resonance Spectra, Stereochemistry and Conformation of Flavan Derivatives. Austral. J. Chem. 17, 632 (1964).

    Article  CAS  Google Scholar 

  22. Conroy, H.: Nuclear Magnetic Resonance in Organic Structural Elucidation. Adv. Organ. Chem. 2, 265 (1960).

    CAS  Google Scholar 

  23. Cooper, R. D. G., L. M. Jackman and B. C. L. Weedon: Stereochemistry of Capsorubin and Synthesis of its Optically Inactive Epimers. Proc. Chem. Soc. (London) 1962, 215.

    Google Scholar 

  24. Corey, E. J., E. M. Philbin and T. S. Wheeler: Stereochemistry of Flavan- 3,4-diols. Tetrahedron Letters 1961, 429.

    Google Scholar 

  25. Cox, J. S. G., E. O. Bishop and R. E. Richards: Proton Resonance Spectra of Some 11-Keto-steroids. J. Chem. Soc. (London) 1960, 5118.

    Google Scholar 

  26. Crombie, L. and J.W. Lown: Proton Magnetic Studies of Rotenone and Related Compounds. J. Chem. Soc. (London) 1962, 775.

    Google Scholar 

  27. Davis, J. B., L. M. Jackman, P. T. Siddons and B. C. L. Weedon: The Structures of Phytoene, Phytofluene, ζ-Carotene and Neurosporene. Proc. Chem. Soc. (London) 1961, 261.

    Google Scholar 

  28. Fräser, R. R.: The Establishment of Configuration of Diels-Alder Adducts by N. M. R. Spectroscopy. Canad. J. Chem. 40, 78 (1962).

    Article  Google Scholar 

  29. Hall, L. D., L. Hough, K. A. McLauchlan and K. Pachler: A Proton Resonance Study of the Conformation of Carbohydrates in Solution. Some Pyranose Derivatives. Chem. and Ind. 1962, 1465.

    Google Scholar 

  30. Hofheinz, W. und H. Grisebach: Zur Biogenese der Makrolide. VII. Die Stereochemie der Mycaminose. Z. Naturforsch. 17B, 355 (1962).

    CAS  Google Scholar 

  31. Jackman, L. M.: Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry. London: Pergamon. 1959.

    Google Scholar 

  32. Jackman, L. M. and S. L. Jensen: Bacterial Carotenoids. IX. The Constitution of the Third Member of the P 481-Group (3,4-Dehydro-rhodopin). Acta. Chem. Scand. 15, 2058 (1961).

    Article  CAS  Google Scholar 

  33. Jackman, L. M. and R. H. Wiley: Studies in Nuclear Magnetic Resonance. Part III. Assignment of Configurations of αβ-Unsaturated Esters and the Isolation of Pure traws-β-Methyl-glutaconic Acid. J. Chem. Soc. (London) 1960, 2886.

    Google Scholar 

  34. Jardetzky, C. D.: Proton Magnetic Resonance Studies on Purines, Pyrimidines, Ribose Nucleosides and Nucleotides. III. Ribose Conformation. J. Amer. Chem. Soc. 82, 229 (1960).

    Article  CAS  Google Scholar 

  35. Johnson, C. E., Jr. and F. A. Bovey: Calculation of Nuclear Magnetic Resonance Spectra of Aromatic Hydrocarbons. J. Chem. Physics 29, 1012 (1958).

    Article  CAS  Google Scholar 

  36. Karplus, M.: The Analysis of Molecular Wave Functions by Nuclear Magnetic Resonance Spectroscopy. J. Physic. Chem. 64, 1793 (1960).

    Article  CAS  Google Scholar 

  37. Karrer, P. and E. Jucker: Carotenoids. New York: Elsevier. 1950.

    Google Scholar 

  38. Kartha, G., G. N. Ramachandran, H. B. Bhat, P. M. Nair, V. K. V. Ragha-van and K. Venkataraman: The Constitution of Morellin. Tetrahedron Letters 1963, 459.

    Google Scholar 

  39. Kevill, D. N., G. A. Coppens, M. Coppens and N. H. Cromwell: Reactions of 2-Bromo-2-(α-halogenobenzyl).i-indanones. J. Organ. Chem. (USA) 29, 382 (1964).

    CAS  Google Scholar 

  40. Lemieux, R. U., R. K. Kullnig, H. J. Bernstein and W. G. Schneider: Configurational Effects on the Proton Magnetic Resonance Spectra of Six-membered Ring Compounds. J. Amer. Chem. Soc. 80, 6098 (1958).

    Article  CAS  Google Scholar 

  41. McLean, S. and Mei-Sie Lin: Ochotensimine: A Novel Benzyl-isoquinoline Alkaloid. Tetrahedron Letters 1964, 3819.

    Google Scholar 

  42. Massicot, J. et J.-P. Marthe: Résonance magnétique nucléaire de produits naturels. III. Étude de quelques dérivés flavoniques et substances apparentées. Bull. soc. chim. France 1962, 1962.

    Google Scholar 

  43. Miyamoto, M., Y. Kawamatsu, M. Shinohara, Y. Asahi, Y. Nakadaira, H. Kakisawa, K. Nakanishi and N. S. Bhacca: Chromose A. Tetrahedron Letters 1963, 693.

    Google Scholar 

  44. Nair, M. D. and R. Adams: The Structure of Ridellic Acid and the Stereochemistry of Necic Acids. J. Amer. Chem. Soc. 83, 922 (1961).

    Article  CAS  Google Scholar 

  45. Pople, J. A., W. G. Schneider and H. J. Bernstein: High Resolution Nuclear Magnetic Resonance, p. 98. New York: McGraw-Hill. 1959.

    Google Scholar 

  46. Roberts, J. D.: An Introduction to the Analysis of Spin-Spin Splitting in High-resolution Nuclear Magnetic Resonance Spectra. New York: W. A. Benjamin. 1961. Nuclear Magnetic Resonance. Applications to Organic Chemistry. New York, Toronto, London: McGraw-Hill. 1959.

    Google Scholar 

  47. Schwarz, J. S. P., A. I. Cohen, W. D. Ollis, E. A. Kaczka and L. M. Jackman: The Extractives of Piscidia erythrina L. I. The Constitution of Ichthynone. Tetrahedron 20, 1317 (1964).

    Article  CAS  Google Scholar 

  48. Shoolery, J. N.: Recent Applications of High Resolution N. M. R. to the Determination of Molecular Structure. Discuss. Faraday Soc. No. 34, 104 (1962).

    Article  Google Scholar 

  49. Shoolery, J.N. and M. T. Rogers: Nuclear Magnetic Resonance Spectra of Steroids. J. Amer. Chem. Soc. 80, 5121 (1958).

    Article  CAS  Google Scholar 

  50. Silverstein, R. M. and G. C. Bassler: Spectrometric Identification of Organic Compounds. New York: Wiley and Sons. 1963.

    Google Scholar 

  51. Slomp, G., Jr. and B. R. McGarvey: Nuclear Magnetic Resonance Studies on 6-Methyl Steroids. J. Amer. Chem. Soc. 81, 2200 (1959).

    Article  Google Scholar 

  52. Slomp, G. and F. A. MacKellar: Nuclear Magnetic Resonance Studies using Pyridine Solutions. J. Amer. Chem. Soc. 82, 999 (1960).

    Article  CAS  Google Scholar 

  53. Slomp, G. and F. A. MacKellar: Nuclear Magnetic Resonance Studies on Some Hydrocarbon Side Chains of Steroids. J. Amer. Chem. Soc. 84, 204 (1962).

    Article  CAS  Google Scholar 

  54. Sternhell, S.: Long-range H’—H’ Spin-Spin Coupling in Nuclear Magnetic Resonance Spectroscopy. Rev. Pure and Appl. Chem. 14, 15 (1964).

    CAS  Google Scholar 

  55. Trenner, N. R., B. H. Arison, D. Taub and N. L. Wendler: Proton Magnetic Resonance Shifts in Steroid D-Homoannulation. Proc. Chem. Soc. (London) 1961, 214.

    Google Scholar 

  56. Woo, P. W. K., H.W.Dion and L. F. Johnson: The Stereochemistry of Chalcose, a Degradation Product of Chalcomycin. J. Amer. Chem. Soc. 84, 1066 (1962).

    Article  CAS  Google Scholar 

  57. Zechmeister, L. und L. v. Cholnoky: Untersuchungen über den Paprika- Farbstoff. X. Citraurin aus Capsanthin. Liebigs Ann. Chem. 530, 291 (1937).

    CAS  Google Scholar 

  58. Zeitschel, O.: Über das Nerol und seine Darstellung aus Linalool. Ber. dtsch. chem. Ges. 39, 1780 (1906).

    Article  CAS  Google Scholar 

  59. Zürcher, R. F.: Protonenresonanzspektroskopie und Steroidstruktur. I. Das C-19-Methylsignal in Funktion der Substituenten. Helv. Chim. Acta 44, 1380 (1961).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Melbourne, Australia

    L. M. Jackman

Authors
  1. L. M. Jackman
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. California Institute of Technology, Pasadena, USA

    L. Zechmeister

Rights and permissions

Reprints and permissions

Copyright information

© 1965 Springer-Verlag/Wien

About this chapter

Cite this chapter

Jackman, L.M. (1965). Some Applications of Nuclear Magnetic Resonance Spectroscopy in Natural Product Chemistry. In: Zechmeister, L. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 23. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7139-4_6

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-7139-4_6

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-7141-7

  • Online ISBN: 978-3-7091-7139-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation