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The Natural Environment and the Biogeochemical Cycles pp 229–254Cite as

Natural Organohalogen Compounds

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Abstract

Over the past decade, marine natural products chemists have demonstrated that marine organisms produce a wide variety of halogenated natural products. The halogenated natural products range in size from simple halomethanes to relatively large and complex toxins. The principal sources of halogenated natural products are marine bacteria, marine algae and sponges, with smaller contributions from other marine invertebrates.

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References

  1. Burkholder, P.R., Pfister, R.M., Leitz, F.M.: Appl. Microbiol. 14, 649 (1966)

    Google Scholar 

  2. Andersen, R.J., Wolfe, MS., Faulkner, D.J.: Marine Biol. 27, 281 (1974)

    Google Scholar 

  3. Fenical, W., Look, S.A.: Personal communication

    Google Scholar 

  4. Mynderse, J.S., Moore, R.E.: J. Org. Chem. 43, 2301 (1978)

    Google Scholar 

  5. Mynderse, J.S., Moore, R.E.: Phytochem. 17, 1325 (1978)

    Google Scholar 

  6. Moore, R.E.: Personal communication

    Google Scholar 

  7. Högberg, M.-E., Thomson, R.H., King, T.J.: J. Chem. Soc, Perkin I, 1696 (1976)

    Google Scholar 

  8. McConnell, O.J.: Ph. D. Thesis, UC San Diego 1978

    Google Scholar 

  9. Fenical, W.: Tetrahedron Lett. 4463 (1974)

    Google Scholar 

  10. Burreson, B.J., Moore, R.E., Roller, P.P.: Tetrahedron 473 (1975). Burreson, B.J., Moore, R.E., Roller, P.P.: Agri. Food Chem. 24, 856 (1976); Woolard, F.X., Moore, R.E., Roller, P.P.: Tetrahedron 32, 2843 (1976)

    Google Scholar 

  11. McConnell, O.J., Fenical, W.: Phytochem. 16, 367 (1977)

    Google Scholar 

  12. Suida, J.F. et al.: J. Am. Chem. Soc. 97, 937 (1975)

    Google Scholar 

  13. McConnell, O.J., Fenical, W.: Tetrahedron Lett. 4159 (1977)

    Google Scholar 

  14. McConnell, O.J., Fenical, W.: Tetrahedron Lett. 1851 (1977)

    Google Scholar 

  15. Rose, A.F., Pettus, J.A., Sims, J.J.: Tetrahedron Lett. 1847 (1977)

    Google Scholar 

  16. Kazlauskas, R. et al.: Tetrahedron Lett. 37 (1977)

    Google Scholar 

  17. Pettus, Jr., J.A., Wing, R.M., Sims, J.J.: Tetrahedron Lett. 41 (1977)

    Google Scholar 

  18. Moore, R.E. in: Marine Natural Products, Chemical and Biological Perspectives, (ed.) P.J. Scheuer, Vol. 1, Academic Press, New York 1978, p. 59

    Google Scholar 

  19. Theiler, R.F., Suida, J.F., Hager, L.P. in: Drugs and Food from the Sea (eds.) P.N. Kaul and C.J. Sindermann, Univ. Oklahoma: Norman 1978, p. 154

    Google Scholar 

  20. Faulkner, D.J. et al.: J. Am. Chem. Soc. 95, 3413 (1973)

    Google Scholar 

  21. Mynderse, J.S., Faulkner, D.J.: Tetrahedron 31, 1963 (1975)

    Google Scholar 

  22. Mynderse, J.S., Faulkner, D.J.: Phytochem. 17, 237 (1978)

    Google Scholar 

  23. Crews, P., Kho, E.: J. Org. Chem. 39, 3303 (1974)

    Google Scholar 

  24. Norton, R.S., Warren, R.G., Wells, R.J.: Tetrahedron Lett., 3905, (1977) and [21] and [22]

    Google Scholar 

  25. Higgs, M.D., Vanderah, D.J., Faulkner, D.J.: Tetrahedron 33, 2775 (1977)

    Google Scholar 

  26. Gonzélez, A.G. et al.: Phytochem. 17, 947 (1978)

    Google Scholar 

  27. Van Engen, D. et al.: Tetrahedron Lett. 29 (1978)

    Google Scholar 

  28. Mynderse, J.S. et al.: Tetrahedron Lett. 2175 (1975)

    Google Scholar 

  29. Mynderse, J.S., Faulkner, D.J.: J. Am. Chem. Soc. 96, 6711 (1974)

    Google Scholar 

  30. Crews, P., Kho-Wiseman, E.: J. Org. Chem. 42, 2812 (1977)

    Google Scholar 

  31. Crews, P.: J. Org. Chem. 42, 2634 (1977)

    Google Scholar 

  32. Stierle, D.B., Wing, R.M., Sims, J.J.: Tetrahedron Lett. 4455 (1976). Kazlauskas, R. et al.: Tetrahedron Lett. 4451 (1976)

    Google Scholar 

  33. Ichikawa, N., Naya, Y., Enomoto, S.: Chem. Lett. 1333 (1974)

    Google Scholar 

  34. Burreson, B.J., Woolard, F.X., Moore, R.E.: Tetrahedron Lett. 2155 (1975)

    Google Scholar 

  35. Burreson, B.J., Woolard, F.X., Moore, R.E.: Chem. Lett. 1111 (1975)

    Google Scholar 

  36. Woolard, F.X. et al.: Tetrahedron Lett. 2367 (1978)

    Google Scholar 

  37. McConnell, O.J., Fenical, W.: J. Org. Chem. 43, 4238 (1978)

    Google Scholar 

  38. Martin, J.D., Darias, J. in: Marine Natural Products: Chemical and Biological Perspectives, (ed.), P.J. Scheuer, Vol. I, Academic Press, New York 1978; p. 125

    Google Scholar 

  39. Irie, T. et al.: Tetrahedron 26, 3271 (1970

    Google Scholar 

  40. Kazlauskas, R. et al.: Aust. J. Chem. 29, 2533 (1976)

    Google Scholar 

  41. Caccamese, S., Rinehart, Jr., K.L. in: Drugs and Food from the Sea- Myth or Reality? (ed. P.N. Kaul and C.J. Sinderman), Univ. Oklahoma, Norman 1978; p. 187

    Google Scholar 

  42. Sims, J.J. et al.: Antimicrob. Agents and Chemother. 7, 320 (1975)

    Google Scholar 

  43. Suzuki, T., Suzuki, M., Kurosawa, E.: Tetrahedron Lett. 3057 (1975)

    Google Scholar 

  44. White, R.H., Hager, L.P. in: The Nature of Seawater (ed. E.D. Goldberg), Dahlem Konferenzen, Berlin 1975, p. 633

    Google Scholar 

  45. Gonzélez, A.G. et al.: Tetrahedron Lett. 1249 (1974)

    Google Scholar 

  46. Gonzélez, A.G. et al.: Tetrahedron 31, 2449 (1975)

    Google Scholar 

  47. Faulkner, D.J.: Phytochemistry 15, 1992 (1976)

    Google Scholar 

  48. Howard, B.M., Fenical, W.: Tetrahedron Lett. 41 (1976)

    Google Scholar 

  49. Sims, J.J. et al.: J. Am. Chem. Soc. 93, 3774 (1971)

    Google Scholar 

  50. Sims, J.J. et al.: Tetrahedron Lett. 195 (1972)

    Google Scholar 

  51. Sims, J.J. et al.: J. Am. Chem. Soc. 95, 972 (1973)

    Google Scholar 

  52. Faulkner, D.J., Stallard, M.O., Ireland, C.: Tetrahedron Lett. 3571 (1974)

    Google Scholar 

  53. Sims, J.J., Lin, G.H.Y., Wing, R.M.: Tetrahedron Lett. 3487 (1974), Gonzélez, A.G. et al.: Tetrahedron Lett. 3051 (1976). Waraszkiewicz, S.M., Erickson, K.L.: ibid. 2003 (1974). See also [36]

    Google Scholar 

  54. Howard, B.M., Fenical, W.: Tetrahedron Lett. 2519 (1976)

    Google Scholar 

  55. Suzuki, M., Kurosawa, E., Irie, T.: Tetrahedron Lett. 4995 (1970), Suzuki, M., Kurosawa, E., Irie, T.: Tetrahedron Lett. 821 (1974)

    Google Scholar 

  56. Gonzélez, A.G. et al.: Tetrahedron Lett. 2499 (1975)

    Google Scholar 

  57. Wratten, S.J., Faulkner, D.J.: J. Org. Chem. 42, 3343 (1977)

    Google Scholar 

  58. Rose, A.F., Sims, J.J.: Tetrahedron Lett. 2935 (1977)

    Google Scholar 

  59. Howard, B.M., Fenical, W.: J. Org. Chem. 42, 2518 (1977)

    Google Scholar 

  60. Fenical, W. et al.: Tetrahedron Lett. 3983 (1975)

    Google Scholar 

  61. Howard, B.M., Fenical, W.: J. Org. Chem. 43, 4401 (1978)

    Google Scholar 

  62. Howard, B.M., Fenical, W.: Tetrahedron Lett. 2453 (1978)

    Google Scholar 

  63. Fattorusso, E. et al.: Gazz. Chim. Ital. 106, 779 (1976)

    Google Scholar 

  64. Fenical, W., Finer, J., Clardy, J.: Tetrahedron Lett. 731 (1976)

    Google Scholar 

  65. Sims, J.J. et al.: Chem. Commun. 470 (1973)

    Google Scholar 

  66. Blunt, J.W. et al.: Tetrahedron Lett. 69 (1978)

    Google Scholar 

  67. Irie, T., Suzuki, M., Masamune, T.: Tetrahedron 24, 4193 (1968)

    Google Scholar 

  68. Cameron, A.F. et al.: J. Chem. Soc. (B) 559 (1969)

    Google Scholar 

  69. Irie, T., Izawa, M., Kurosawa, E.: Tetrahedron 26, 851 (1970)

    Google Scholar 

  70. Kurosawa, E. et al.: Tetrahedron Lett. 3857 (1973)

    Google Scholar 

  71. Furusaki, A. et al.: Tetrahedron Lett. 4579 (1973)

    Google Scholar 

  72. Kurosawa, E., Fukuzawa, A., Irie, T.: Tetrahedron Lett. 4135 (1973)

    Google Scholar 

  73. Fenical, W., Gifkins, K.B., Clardy, J.: Tetrahedron Lett. 1507 (1974)

    Google Scholar 

  74. Waraszkiewicz, S.M., Sun, H.H., Erickson, K.L.: Tetrahedron Lett. 3021 (1976)

    Google Scholar 

  75. Sun, H.H., Waraszkiewicz, S.M., Erickson, K.L.: Tetrahedron Lett. 4227 (1976)

    Google Scholar 

  76. For a more complete review see: Faulkner, D.J. in: Top. Antibiotic Chem. (ed. P.G. Sammes), Vol. 2, Ellis Horwood, Chichester, U.K. 1978, p. 39

    Google Scholar 

  77. Pedersen, M., Saenger, P., Fries, L.: Phytochem. 13, 2273 (1974)

    Google Scholar 

  78. Glombitza, K.-W., Stoffelen, H.: Planta Med. 22, 391 (1972)

    Google Scholar 

  79. Saito, T., Ando, Y.: Nippon Kaguka Zasshi 76, 478 (1955)

    Google Scholar 

  80. Glombitza, K.-W. et al.: Planta Med. 25, 105 (1974)

    Google Scholar 

  81. Stoffelen, H. et al.: Planta Med. 22, 396 (1972)

    Google Scholar 

  82. Chautraine, J.-M., Combaut, G., Teste, J.: Phytochem. 12, 1793 (1973)

    Google Scholar 

  83. Chevolot-Magneur, A.-M. et al.: Phytochem. 15, 767 (1976)

    Google Scholar 

  84. Ohta, K., Takagi, M.: Phytochem. 16, 1085 (1977)

    Google Scholar 

  85. Brennan, M.R., Erickson, K.L.: Tetrahedron Lett. 1637 (1978)

    Google Scholar 

  86. Carter, G.T. et al.: Tetrahedron Lett. 4479 (1978)

    Google Scholar 

  87. Wratten, S.J., Faulkner, D.J.: J. Amer. Chem. Soc. 99, 7367 (1977)

    Google Scholar 

  88. Wratten, S.J. et al.: Tetrahedron Lett. 1391 (1978)

    Google Scholar 

  89. Wratten, S.J., Faulkner, D.J.: Tetrahedron Lett. 1395 (1978)

    Google Scholar 

  90. Hofheinz, W., Oberhansli, W.E.: Helv. Chim. Acta. 60, 660 (1977)

    Google Scholar 

  91. Charles, C. et al.: Tetrahedron Lett. 1519 (1978)

    Google Scholar 

  92. Kazlauskas, R. et al.: Tetrahedron Lett. 3183 (1977)

    Google Scholar 

  93. Kazlauskas, R., Murphy, P.T., Wells, R.J.: Tetrahedron Lett. 4945 (1978)

    Google Scholar 

  94. Sharma, G.M., Vig, B.: Tetrahedron Lett. 1715 (1972)

    Google Scholar 

  95. Kazlauskas, R., Murphy, P.T., Wells, R.J.: Tetrahedron Lett. 4949 (1978)

    Google Scholar 

  96. Sharma, G.M., Burkholder, P.R.: Tetrahedron Lett. 4147 (1967)

    Google Scholar 

  97. Sharma, G.M., Vig, B., Burkholder, P.R.: J. Org. Chem. 35, 2823 (1970)

    Google Scholar 

  98. Andersen, R.J., Faulkner, D.J.: Tetrahedron Lett. 1175 (1973)

    Google Scholar 

  99. Fattorusso, E., Minale, L., Sodano, G.: J. Chem. Soc. Perkin I, 16 (1972). Fulmore, W. et al.: Tetrahedron Lett. 4551 (1970)

    Google Scholar 

  100. Minale, L. et al.: Chem. Commun. 674 (1972)

    Google Scholar 

  101. Stempien, Jr. et al. in: Food-Drugs from the Sea Proc., Mar. Techn. SOC. 1972; p. 105

    Google Scholar 

  102. Krejcarek, G.E. et al.: Tetrahedron Lett. 507 (1975)

    Google Scholar 

  103. Moody, K. et al.: J. Chem. Soc. Perkin I, 18 (1972). (Structure confirmed by X-ray: J. Clardy, personal communication)

    Google Scholar 

  104. Borders, D.B., Morton, G.O., Wetzel, E.R.: Tetrahedron Lett. 2709 (1974)

    Google Scholar 

  105. Schmitz, F.J.: IUPAC Symp. Marine Nat. Prod. Sorrento 1978

    Google Scholar 

  106. Forenza, S. et al.: Chem. Commun. 1129 (1971)

    Google Scholar 

  107. Garcia, E.E., Benjamin, L.E., Fryer, R.I.: Chem. Commun. 78 (1973). (The structure of oroidin has been confirmed by X-ray analysis: J. Clardy, personal communication)

    Google Scholar 

  108. Unpublished research from this laboratory

    Google Scholar 

  109. Sharma, G.M., Burkholder, P.R.: Chem. Commun. 151 (1971)

    Google Scholar 

  110. Van Lear, G.E., Morton, G.O., Fulmor, W.: Tetrahedron Lett. 299 (1973)

    Google Scholar 

  111. Raverty, W.D., Thomson, R.H., King, T.J.: J. Chem. Soc. Perkin I, 1204 (1977)

    Google Scholar 

  112. Andersen, R.J.: Tetrahedron Lett. 2541 (1978)

    Google Scholar 

  113. Schmitz, F.J., Gopichand, Y.: Tetrahedron Lett. 3637 (1978)

    Google Scholar 

  114. Cimino, G., De Stefano, S.: Tetrahedron Lett. 1325 (1977)

    Google Scholar 

  115. Burks, J.E. et al.: Acta Cryst. 33, 704 (1977)

    Google Scholar 

  116. Wratten, S.J. et al.: J. Amer. Chem. Soc. 99, 2824 (1977)

    Google Scholar 

  117. Wratten, S.J. et al.: Tetrahedron Lett. 1559 (1977)

    Google Scholar 

  118. Faulkner, D.J., Ireland, C. in: Marine Natural Products Chemistry (eds. D.J. Faulkner and W. Fenical) Plenum, New York 1977, p. 23

    Google Scholar 

  119. Stallard, M.O., Faulkner, D.J.: Comp. Biochem. Physiol. 49B, 25 (1974)

    Google Scholar 

  120. Yamamura, S., Hirata, Y.: Tetrahedron 19, 1485 (1963)

    Google Scholar 

  121. Matsuda, H. et al.: Chem. Commun. 898 (1967)

    Google Scholar 

  122. Pettit, G.R. et al.: J. Org. Chem. 43, 4685 (1978)

    Google Scholar 

  123. Pettit, G.R. et al.: J. Amer. Chem. Soc. 99, 262 (1977)

    Google Scholar 

  124. McDonald, F.J. et al.: J. Org. Chem. 40, 665 (1975)

    Google Scholar 

  125. Kinnel, R. et al.: Tetrahedron Lett. 3913 (1977)

    Google Scholar 

  126. Kato, Y., Scheuer, P.J.: Pure Appl. Chem. 41, 1 (1975)

    Google Scholar 

  127. Rose, A.F. et al.: J. Amer. Chem. Soc. 100, 7665 (1978)

    Google Scholar 

  128. Hashimoto, Y. et al.: Bull. Jap. Soc. Sci. Fish. 33, 661 (1967)

    Google Scholar 

  129. Kosuge, T. et al.: Tetrahedron Lett. 2545 (1972)

    Google Scholar 

  130. Personal communication from Y. Shimizu, who has translated Japanese reports

    Google Scholar 

  131. Baker, J.T.: Pure Appl. Chem. 48, 35 (1976) (review)

    Google Scholar 

  132. Ashworth, R.B., Cormier, M.J.: Science 155, 1588 (1967)

    Google Scholar 

  133. Higa, T.: Amer. Chem. Soc. Meeting, Honolulu 1979

    Google Scholar 

  134. Sheikh, Y.M., Djerassi, C.: Experientia 31, 265 (1975)

    Google Scholar 

  135. Higa, T., Scheuer, P.J.: Tetrahedron 31, 2379 (1975)

    Google Scholar 

  136. Higa, T., Scheuer, P.J. in: NATO Conf. Marine Nat. Prod. (eds. D.J. Faulkner and W. H. Fenical). Plenum, New York 1977, p. 35

    Google Scholar 

  137. Higa, T., Scheuer, P.J.: Naturwissenschaften 62, 395 (1975)

    Google Scholar 

  138. Siuda, J.F., DeBernardis, J.F.: Lloydia 36, 107 (1973)

    Google Scholar 

  139. Marius, J.S.C.: Onderstepoort J. Vet. Sci. 20, 67 (1944)

    Google Scholar 

  140. Ward, P.F.V., Hall, R.J., Peters, R.A.: Nature 201, 611 (1964)

    Google Scholar 

  141. Thieler, R. et al.: Science 202, 1094 (1978)

    Google Scholar 

  142. Wolinsky, L.E., Faulkner, D.J.: J. Org. Chem. 41, 597 (1976)

    Google Scholar 

  143. Faulkner, D.J., Stallard, M.O.: Tetrahedron Lett. 1171 (1973)

    Google Scholar 

  144. Sims, J.J., Rose, A.F., Izac, R.R. in: Marine Natural Products, Chemical and Biological Perspectives (ed. P.J. Scheuer) Vol. 2, Academic Press, New York 1978, p. 297

    Google Scholar 

  145. Lovelock, J.E.: Nature 256, 193 (1975)

    Google Scholar 

  146. Fenical, W.H.: Personal communication

    Google Scholar 

  147. Crews, P. et al.: Phytochemistry 15, 1707 (1976)

    Google Scholar 

  148. Unpublished observations - this laboratory

    Google Scholar 

  149. Ohta, K., Takagi, M.: Phytochemistry 16, 1062 (1977)

    Google Scholar 

  150. Rinehart, Jr. et al. in: Dahlem Conf. Rep. Nature of Sea Water, (ed. E.D. Goldberg) Abakon Verlags-Ges., Berlin 1975, p. 651

    Google Scholar 

  151. Stallard, M.O., Faulkner, D.J.: Comp. Biochem. Physiol. 49B, 37 (1974)

    Google Scholar 

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    D. J. Faulkner

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Faulkner, D.J. (1980). Natural Organohalogen Compounds. In: The Natural Environment and the Biogeochemical Cycles. The Handbook of Environmental Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-24940-6_9

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