Skip to main content
Log in

Polycyclic diterpenoids biogenetically related to the cembranoids

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

This review describes cyclocembrane compounds isolated from plants, marine organisms, and insects. A systematization of cyclized diterpenoids according to the types of carbon skeletons is given.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. J. D. Bu'lock, The Biosynthesis of Natural Products. An Introduction to Secondary Metabolism, McGraw-Hill, London (1965), pp. 57–149.

    Google Scholar 

  2. W. G. Dauben, W. F. Thiessen and P. R. Resnick, J. Am. Chem. Soc.,84, 2015 (1962).

    Google Scholar 

  3. H. Kobayashi and S. Akiyoshi, Bull. Chem. Soc. Jpn.,35, 1044 (1962).

    Google Scholar 

  4. A. J. Weinheimer, C. W. I. Chang, and J. A. Matson, Fortschr. Chem. Org. Naturst,36, 285 (1979).

    Google Scholar 

  5. H. Erdtman, T. Norin, M. Sumimoto, and A. Morrison, Tetrahedron Lett., 3879 (1964).

  6. E. N. Shmidt, N. K. Kashtanova, and V. A. Pentegova, Khim. Prir. Soedin., 694 (1970).

  7. V. A. Raldugin, L. I. Demenkova, and V. A. Pentegova, Khim. Prir. Soedin, 677 (1984).

  8. V. D. Patil, U. R. Nayak and S. Dev, Tetrahedron,29, 341 (1973).

    Google Scholar 

  9. A. J. Blackman, B. F. Bowden, J. C. Coll, B. Frick, M. Mahendran, and S. I. Mitchell, Aust. J. Chem.,35, 1873 (1982).

    Google Scholar 

  10. A. I. Birch, W. V. Brown, I. E. T. Corrie, and B. P. Moore, J. Chem. Soc. Perkin Trans. I, 2653 (1972).

  11. S. Carmely, A. Groweiss, and A. Kashman, J. Org. Chem.,46, 4279 (1981).

    Google Scholar 

  12. B. Karlsson, A.-M. Pilotti, A.-Ch. Söderholm, T. Norin, S. Sundin, and M. Sumimoto, Tetrahedron,34, 2349 (1978).

    Google Scholar 

  13. S. Hasegawa and Y. Hirose, Phytochemistry,24, 2041 (1985).

    Google Scholar 

  14. A. A. Adesomoju, J. I. Okogun, M. P. Cava, and P. J. Carroll, Heterocycles,20, 2125 (1983).

    Google Scholar 

  15. A. A. Adesomoju and J. I. Okogun, J. Nat. Prod.,47, 308 (1984).

    Google Scholar 

  16. B. A. Burke, W. R. Chan, V. A. Honkon, J. F. Blount, and P. S. Manhand, Tetrahedron,36, 3489 (1980).

    Google Scholar 

  17. E. Fujita, K. Fuji, Y. Nagao, and M. Node, Bull. Inst. Chem. Res., Kyoto Univ.,52, 385 (1979).

    Google Scholar 

  18. B. Lythgoe, K. Nakanishi, and S. Uyeo, Proc. Chem. Soc. (London), 301 (1964).

  19. Lukas, Arch. Pharm.,56, 145 (1856).

    Google Scholar 

  20. E. Graf and H. Boeddeker, Arch. Pharm.,289, 364 (1956).

    Google Scholar 

  21. J. M. Baxter, B. Lythgoe, B. Scales, and S. Trippett, Proc. Chem. Soc. (London), 9 (1958).

  22. J. M. Baxter, B. Lythgoe, B. Scales, R. M. Scrowiston, and S. Trippett, J. Chem. Soc., 2964 (1962).

  23. D. H. Eyre, J. M. Harrison, R. M. Scrowston, and B. Lythgoe, Proc. Chem. Soc. (London), 271 (1963).

  24. M. Kurono, Y. Nakadaira, S. Onuma, K. Sasaki, and K. Nakanishi, Tetrahedron Lett., 2153 (1963).

  25. K. Ueda, S. Ueyo, Y. Yamamoto, and Y. Maki, Tetrahedron Lett., 2176 (1963).

  26. B. Lythgoe, K. Nakanishi, and S. Uyeo, Proc. Chem. Soc. (London), 301 (1964).

  27. M. Dukes, D. H. Eyre, J. W. Harrison, and B. Lythgoe, Tetrahedron Lett., 4765 (1965).

  28. M. Kurono, Y. Maki, N. Nakanishi, M. Ohashi, K. Ueda, S. Uyeo, C. M. Woods, and Y. Yamamoto, Tetrahedron Lett., 1917 (1965).

  29. M. Shiro, T. Sato, H. Koyama, Y. Maki, K. Nakanishi, and S. Uyeo, J. Chem. Soc., Chem. Commun., 97 (1966).

  30. M. Duke, D. H. Eyre, J. W. Harrison, R. M. Scrowstone, and B. Lythgoe, J. Chem. Soc. (C), 448 (1967).

  31. W. R. Chan, T. G. Halsall, G. H. Hornby, A. W. Oxford, W. Sabel, K. Bjomer, G. Ferguson, and J. M. Robertson, J. Chem. Soc., Chem. Commun.,923 (1966).

  32. M. Miyazaki, K. Shimizu, H. Mishime, and M. Kuraboyashi, Chem. Pharm. Bull.,16, 546 (1968).

    Google Scholar 

  33. H.-C. Chiang, M. C. Woods, K. Nakanishi, and Y. Nakadaira, J. Chem. Soc., Chem. Commun., 1201 (1967).

  34. M. C. Woods, H.-C. Chiang, Y. Nakadaira, and K. Nakanishi, J. Am. Chem. Soc.,20, 522 (1968).

    Google Scholar 

  35. D. H. Della Casa de Marcano and T. G. Halsall, J. Chem. Soc., Chem. Commun.,21, 1282 (1969).

    Google Scholar 

  36. D. H. Della Casa de Marcano and T. G. Halsall, J. Chem. Soc., Chem. Commun.,21, 1381 (1970).

    Google Scholar 

  37. D. H. Della Casa de Marcano and T. G. Halsall, J. Chem. Soc., Chem. Commun., 1382 (1970).

  38. D. H. Della Casa de Marcano and T. G. Halsall, J. Chem. Soc., Chem. Commun., 365 (1975).

  39. M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, and A. McPhail, J. Am. Chem. Soc.,93, 2325 (1971).

    Google Scholar 

  40. R. W. Miller, R. G. Powell, C. R. Smith, E. Arnold, and J. Clardy, J. Org. Chem.,46, 1469 (1981).

    Google Scholar 

  41. G. Chauviere, D. Guenard, C. Pascard, F. Picot, P. Potier, and T. Pranget, J. Chem. Soc., Chem. Commun., 495 (1982).

  42. R. W. Miller, R. G. Powell and C. R. Smith, US Patent No. 4,206,221 [Chem. Abstr., No. 17, 168465 (1980)].

  43. J. L. McLaughlin, R. W. Miller, R. G. Powell, and C. R. Smith, Jr., J. Nat. Prod.,44, 312 (1981).

    Google Scholar 

  44. C. S. Swindell and S. J. Salms, Tetrahedron,25, 3801 (1984).

    Google Scholar 

  45. N. Harribert, B. Siegfried, S. Walfgang, and J. Martin, Angew. Chem.,96, 303 (1984).

    Google Scholar 

  46. H. Hagaoka, K. Ohsawa, T. Takata, and Y. Yamata, Tetrahedron Lett.,25, 5389 (1984).

    Google Scholar 

  47. M. J. Begley, C. B. Jackson, and G. Pattenden, Tetrahedron Lett.,26, 3397 (1985).

    Google Scholar 

  48. I. Wahlberg, A.-M. Eklung, J. Nishida, and C. R. Enzell, Tetrahedron Lett.,24, 843 (1983).

    Google Scholar 

  49. O. Kennard, D. G. Watson, L. R. di Sanseverino, B. Tursch, R. Bosmans, and C. Djerassi, Tetrahedron Lett.,24, 2879 (1968).

    Google Scholar 

  50. G. Aranda, J. C. Braekman, J. Call, D. Daloze, and B. Tursch, Colloq. Int. CNRS (1980), p. 103.

  51. Y. Uchio, H. Naboya, M. Nakyama, S. Hayashi, and T. Hase, Tetrahedron Lett.,22, 1689 (1981).

    Google Scholar 

  52. R. Kazlauskas, P. T. Murphy, R. J. Wells and P. Schönholzer, Tetrahedron Lett.,52, 4643 (1977).

    Google Scholar 

  53. T. C. Hochlowski and D. J. Faulkner, Tetrahedron Lett.,21, 4055 (1980).

    Google Scholar 

  54. Y. Kashman, Tetrahedron Lett.,21, 879 (1980).

    Google Scholar 

  55. V. A. Raldugin, S. A. Shevtsov, V. I. Mamatyuk, and V. A. Pentegova, Sibirskogo Otd. Akad. Nauk, SSSR, Ser. Khim. Nauk, Issue No. 15, Series No. 1, p. 98 (1986).

  56. D. B. Stierle, B. Carte, D. J. Faulkner, B. Tagle, and J. Clardy, J. Am. Chem. Soc.,102, 5088 (1980).

    Google Scholar 

  57. S. J. Selover, P. Creras, B. Tagle, and J. Clardy, J. Org. Chem.,46, 964 (1981).

    Google Scholar 

  58. J. E. Burks, D. Van der Helm, C. Y. Chonge and L. C. Ciereszko, Acta Crystallogr., Sect. B,B33, 704 (1972).

    Google Scholar 

  59. A. J. Wratten, D. J. Faulkner, K. Hirotsu, and J. Clardy, J. Am. Chem. Soc.,99, 2824 (1977).

    Google Scholar 

  60. S. J. Wratten and D. J. Faulkner, Tetrahedron,35, 1907 (1979).

    Google Scholar 

  61. S. J. Wratten, W. Fenical, D. J. Faulkner, and T. C. Wekell, Tetrahedron Lett.,18, 1559 (1977).

    Google Scholar 

  62. B. N. Ravi, J. F. Marwood, and R. I. Wells, Aust. J. Chem.,33, 2307 (1980).

    Google Scholar 

  63. S. H. Grode, T. R. James, and J. H. Cardellina, Tetrahedron Lett.,24, 691 (1983).

    Google Scholar 

  64. J. Yao, J. Qian, H. Fan, K. Shih, S. Huang, Y. Liin, and K. Long, Zhongshan Daxue Xuebao, Ziran Kexueban, 83 (1984) (Chem. Abstr.,101, 211491c).

  65. A. Clasters, A. Ahond, P. Laboute, C. Poupat, and P. Potier, J. Nat. Prod.,47, 155 (1984).

    Google Scholar 

  66. A. Clasters, P. Laboute, A. Ahond, C. Poupat, and P. Potier, J. Nat. Prod.,47, 162 (1984).

    Google Scholar 

  67. S. A. Look, W. Fenical, D. van Engen, and J. Clardy, J. Am. Chem. Soc.,106, 5026 (1984).

    Google Scholar 

  68. G. H. Prestwich, S. P. Tanis, J. P. Springer, and J. Clardy, J. Am. Chem. Soc.,98, 6061 (1976).

    Google Scholar 

  69. J. C. Braekman, D. Daloze, A. Dupont, J. Pasteels, B. Tursch, J. P. Declerq, G. Germain, and M. van Meerssche, Tetrahedron Lett.,21, 27 (1980).

    Google Scholar 

  70. R. Baker, A. J. Organ, K. Prout, and R. Jones, Tetrahedron Lett.,25, 579 (1984).

    Google Scholar 

  71. G. D. Prestwich, S. P. Tanis, F. G. Pilkiewicz, I. Miura, and K. Nakanishi, J. Am. Chem. Soc.,98, 6062 (1976).

    Google Scholar 

  72. J. Vrkoc, M. Budesinsky, and P. Sedmera, Collect. Czech. Chem. Commun.,43, 1125 (1978).

    Google Scholar 

  73. J. Vrkoc, M. Budesinsky, and P. Sedmera, Collect. Czech. Chem. Commun.,43, 2473 (1978).

    Google Scholar 

  74. G. D. Prestwich, Experientia,34, 682 (1978).

    Google Scholar 

  75. J. C. Braekman, D. Daloze, A. Dupont, J. M. Arrieta, C. Piccini-Leopardi, G. Germain, and M. van Meerssche, Bull Soc. Chim. Belg.,92, 111 (1983).

    Google Scholar 

  76. G. D. Prestwich, S. G. Spanton, and Y. P. Tho, Tetrahedron Lett.,22, 1563 (1981).

    Google Scholar 

  77. A. Dupont, Y. P. Braekman, D. Daloze, J. M. Posdeels and B. Tursch, Bull Soc. Chim. Belg.,90, 485 (1981).

    Google Scholar 

  78. J. C. Braekman, D. Daloze, A. Dupont, J. M. Posteels, and R. Ottinger, Bull. Soc. Chim. Belg.,93, 291 (1984).

    Google Scholar 

  79. G. D. Prestwich, B. A. Solheim, J. Clardy, F. G. Pilkiewicz, J. Miura, S. P. Tanis, and K. Nakanishi, J. Am. Chem. Soc.,99, 8082 (1977).

    Google Scholar 

  80. G. D. Prestwich, S. H. Goh, and Y. P. Tho, Experientia,37, 11 (1981).

    Google Scholar 

  81. G. D. Prestwich, J. W. Louher, and M. S. Collins, Tetrahedron Lett., 3827 (1979).

  82. S. Cerrini, D. Lamba, D. Budesinsky, and I. Valteroa, in: 11th Conference on Isoprenoids. Abstracts of Papers, Jahranka (Poland), September 16–21 (1985), p. 22.

  83. G. D. Prestwich, S. G. Spanton, L. M. Louher, and J. Vrkoc, J. Am. Chem. Soc.,102, 6825 (1980).

    Google Scholar 

Download references

Authors

Additional information

Novosibirsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 327–342, May–June, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Raldugin, V.A., Shevtsov, S.A. Polycyclic diterpenoids biogenetically related to the cembranoids. Chem Nat Compd 23, 269–281 (1987). https://doi.org/10.1007/BF00600822

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00600822

Keywords

Navigation