Skip to main content
SpringerLink
Log in

Electrophilic heterocyclization of unsaturated carboxylic acids in the synthesis of lactones (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Data on the electrophilic-heterocyclization reactions of γ, δ- and δ, ε-unsaturated carboxylic acids are correlated. The use of this reaction for the synthesis of substituted mono-, bi-, tri-, and polycyclic γ- and δ-lactones is demonstrated. Data on the regioselectivity of the addition of electrophiles and the stereochemistry of the resulting cyclization products are presented.

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

Access this article

Log in via an institution

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. Yu. I. Gevaza and V. I. Staninets, Khim. Geterotsikl. Soedin., No. 11, 1443 (1982).

    Google Scholar 

  2. Yu. I. Gevaza and V. I. Staninets, Khim. Geterotsikl. Soedin., No. 4, 435 (1985).

    Google Scholar 

  3. Yu. I. Gevaza and V. I. Staninets, Khim. Geterotsikl. Soedin., No. 3, 291 (1986).

    Google Scholar 

  4. R. Fittig and E. Hjelt, Annalen, 216, 61 (1983).

    Google Scholar 

  5. V. I. Staninets and E. A. Shilov, Usp. Khim., 40, 491 (1971).

    Google Scholar 

  6. M. D. Dowle and D. I. Davies, Chem. Soc. Rev., 8, 171 (1979).

    Google Scholar 

  7. P. de la Mare and R. Bolton, Electrophilic Addition to Unsaturated Systems [Russian translation], Mir, Moscow (1968), p. 172.

    Google Scholar 

  8. P. Bartlett, Contemporary Trends in Organic Synthesis [Russian translation], Mir, Moscow (1986), p. 256.

    Google Scholar 

  9. W. E. Barnett and J. C. McKenna, Tetrahedron Lett., No. 28, 2595 (1971).

    Google Scholar 

  10. W. E. Barnett and W. H. Sohn, Tetrahedron Lett., No. 18, 1777 (1972).

    Google Scholar 

  11. W. E. Barnett and W. H. Sohn, Chem. Commun., No. 8, 472 (1972).

    Google Scholar 

  12. E. J. Corey and T. Hase, Tetrahedron Lett., No. 4, 335 (1979).

    Google Scholar 

  13. R. C. Cambie, K. S. Ng, P. S. Rulledge, and P. D. Wootgate, Aust. J. Chem., 32, 2793 (1979).

    Google Scholar 

  14. D. Goldsmith, D. Liotta, Ch. Lee, and G. Zima, Tetrahedron Lett., No. 50, 4801 (1979).

    Google Scholar 

  15. G. A. Tolstikov and U. M. Dzhemilev, Khim. Geterotsikl. Soedin., No. 2, 147 (1980).

    Google Scholar 

  16. B. Damin, A. Forestiere, J. Garapon, and B. Silion, J. Org. Chem., 46, 3552 (1981).

    Google Scholar 

  17. J. V. Comasseto and N. Petragnani, Synth. Commun., 13, 889 (1983).

    Google Scholar 

  18. T. Umemoto, U. Kyriy, and S. Nakayama, Tetrahedron Lett., No. 11, 1169 (1982).

    Google Scholar 

  19. K. C. Nicolaou, W. E. Claremon, W. E. Barnette, and S. P. Seitz, J. Am. Chem. Soc., 101, 3704 (1979).

    Google Scholar 

  20. D. L. J. Clive, Ch. G. Russell, G. Chittattu, and A. Singh, Tetrahedron, 36, 1399 (1980).

    Google Scholar 

  21. J. W. Lown and A. V. Joshua, Can. J. Chem., 55, 122 (1977).

    Google Scholar 

  22. G. J. O'Malley and M. P. Cava, Tetrahedron Lett., No. 50, 6159 (1985).

    Google Scholar 

  23. P. A. Bartlett and J. Myerson, J. Am. Chem. Soc., 100, 3950 (1978).

    Google Scholar 

  24. N. J. Barnes, A. H. Davidson, L. R. Hughes, G. Procter, and V. Rajcoomar, Tetrahedron Lett., No. 22, 1751 (1981).

    Google Scholar 

  25. V. JÄger, H. J. Günther, Tetrahedron Lett., No. 29, 2543 (1977).

    Google Scholar 

  26. P. A. Bartlett, D. P. Richardson, and J. Myerson, Tetrahedron, 40, 2317 (1984).

    Google Scholar 

  27. D. R. Williams, B. A. Barner, K. Nishitani, and J. G. Phillips, J. Am. Chem. Soc., 104, 4708 (1982).

    Google Scholar 

  28. B. B. Snider and M. J. Johnston, Tetrahedron Lett., No. 45, 5497 (1985).

    Google Scholar 

  29. S. Tsuboi, K. Muranaka, H. Fujita, K. Seko, and A. Takeda, Heterocycles, 21, 602 (1984).

    Google Scholar 

  30. R. N. Uoung, W. Coombs, U. Guindon, J. Rokach, D. Ethier, and R. Hall, Tetrahedron, No. 49, 4933 (1981).

    Google Scholar 

  31. A. R. Chamberlin, M. Dezube, and P. Dussault, Tetrahedron Lett., No. 46, 4611 (1981).

    Google Scholar 

  32. A. R. Chamberlin, M. Dezube, P. Dussault, and M. C. McMills, J. Am. Chem. Soc., 105, 5819 (1983).

    Google Scholar 

  33. P. A. Bartlett, D. J. Tansella and J. E. Barstow, J. Org. Chem., 47, 3941 (1982).

    Google Scholar 

  34. U. Yamamoto, W. Ito and K. Maruyama, Chem. Commun., No. 16, 1131 (1985).

    Google Scholar 

  35. U. Ohfune and N. Kurokawa, Tetrahedron Lett., No. 43, 5307 (1985).

    Google Scholar 

  36. J. K. Lee and T. Kaneko, Bull. Chem. Soc., Jpn., 46, 2924 (1973).

    Google Scholar 

  37. J. T. Welch and J. S. Samartino, J. Org. Chem., 50, 3663 (1985).

    Google Scholar 

  38. U. Hanzawa, K. Kawagoe, K. Kawada, and U. Kobayashi, Chem. Pharm. Bull., 33, 2579 (1985).

    Google Scholar 

  39. T. Morikawa, J. Kumadoki, and M. Shiro, Chem. Pharm. Bull., 33, 5144 (1985).

    Google Scholar 

  40. K. Tanaka, M. Teraychi, and A. Kaji, Chem. Lett., No. 3, 351 (1982).

    Google Scholar 

  41. V. I. Staninets, Yu. V. Melika, and E. A. Shilov, Dokl. Akad. Nauk SSSR, No. 187, 109 (1969).

    Google Scholar 

  42. A. T. Do Amaral and L. Do Amaral, J. Org. Chem., No. 9, 1623 (1976).

    Google Scholar 

  43. O. A. El Seoud, A. T. Do Amaral, and M. M. Moura, J. Org. Chem., 39, 1915 (1975).

    Google Scholar 

  44. M. J. De Almeida, A. T. Do Amaral, and L. Do Amaral, J. Chem. Soc., Perkin 2, No. 12, 1953 (1984).

    Google Scholar 

  45. S. Takano, N. Sato, M. Akiyama, and K. Ogasawara, Heterocycles, 23, 2859 (1985).

    Google Scholar 

  46. V. I. Staninets and Yu. I. Gevaza, Ukr. Khim. Zh., 39, 699 (1973).

    Google Scholar 

  47. L. Do Amaral and S. C. Melo, J. Org. Chem., 38, 800 (1973).

    Google Scholar 

  48. S. Uemura, A. Toshimitsu, T. Aoai, and M. Okano, Tetrahedron Lett., No. 16, 1533 (1980).

    Google Scholar 

  49. A. Toshimitsu, T. Aoai, H. Owada, S. Uemura, and M. Okano, Tetrahedron, 41, 5301 (1985).

    Google Scholar 

  50. M. Kato, M. Kagejama, and A. Uoshikoshi, J. Chem. Soc., Perkin 1, No. 11, 1305 (1977).

    Google Scholar 

  51. M. Kato, M. Kageyama, R. Tanaka, K. Kuwahara, and A. Uoshikoshi, J. Org. Chem., 40, 1932 (1975).

    Google Scholar 

  52. K. C. Nicolaou, N. A. Petasis, and D. A. Claremon, Tetrahedron, 41, 4835 (1985).

    Google Scholar 

  53. T. A. Degurko and V. I. Staninets, Dokl. Akad. Nauk Ukr. SSR, Ser. B, No. 4, 345 (1973).

    Google Scholar 

  54. K. Spencer, R. E. Karen, L. T. Anthony, and O. M. Raphael, Tetrahedron Lett., No. 15, 1803 (1985).

    Google Scholar 

  55. Y. Tamaru, M. Mizutani, Y. Eurakawa, S. Kawamura, Z. Yoshida, K. Yanagi, and M. Minobe, J. Am. Chem. Soc., 106, 1079 (1984).

    Google Scholar 

  56. R. A. Amos and J. A. Katzenellenbogen, J. Org. Chem., 43, 560 (1978).

    Google Scholar 

  57. G. A. Krafft and J. A. Katzenellenbogen, J. Am. Chem. Soc., 103, 5459 (1981).

    Google Scholar 

  58. M. Yamamoto, Chem. Commun., No. 15, 649 (1978).

    Google Scholar 

  59. T. Toru, S. Fujita, M. Saito, and E. Maekawa, J. Chem. Soc., Perkin 1, No. 11, 1999 (1986).

    Google Scholar 

  60. C. Lambert, K. Utimoto, and H. Nozaki, Tetrahedron Lett., No. 46, 5323 (1984).

    Google Scholar 

  61. N. Yanagihara, C. Lambert, K. Iritani, K. Utimoto, and H. Nozaki, J. Am. Chem. Soc., 108, 2753 (1986).

    Google Scholar 

  62. M. J. Sofia, P. K. Chakravarty, and J. A. Katzenellenbogen, J. Org. Chem., 48, 3318 (1983).

    Google Scholar 

  63. M. J. Sofia and J. A. Katzenellenbogen, J. Org. Chem., 50, 2331 (1985).

    Google Scholar 

  64. M. A. Oliver and R. D. Gandour, J. Org. Chem., 49, 558 (1984).

    Google Scholar 

  65. M. Yamamoto, J. Chem. Soc., Perkin 1, No. 2, 582 (1981).

    Google Scholar 

  66. S. Braverman and D. Reisman, Tetrahedron Lett., No. 20, 1753 (1977).

    Google Scholar 

  67. S. W. Rollinson, R. A. Amos, and J. A. Katzenellenbogen, J. Am. Chem. Soc., 103, 4114 (1981).

    Google Scholar 

  68. A. Rouessac, F. Rouessac, and H. Zamarlik, Tetrahedron Lett., No. 28, 2641 (1981).

    Google Scholar 

  69. F. Rouessac and H. Zamarlik, Tetrahedron Lett., No. 28, 2643 (1981).

    Google Scholar 

  70. Yu. A. Arbuzov, V. T. Ivanov, M. N. Kolosov, Yu. A. Ovchinnikov, and M. M. Shemyakin, Zh. Obshch. Khim., 34, 1090 (1964).

    Google Scholar 

  71. D. L. J. Clive and G. Chittattu, Chem. Commun., No. 14, 484 (1977).

    Google Scholar 

  72. K. C. Nicolaou, Tetrahedron, 37, 4097 (1981).

    Google Scholar 

  73. J. Klein, J. Am. Chem. Soc., 81, 3611 (1959).

    Google Scholar 

  74. P. A. Grieco, N. Marinovic, and M. Miyashita, J. Org. Chem., 40, 1670 (1975).

    Google Scholar 

  75. S. D. Burke, W. F. Fobare, and D. M. Armistead, J. Org. Chem., 47, 3348 (1982).

    Google Scholar 

  76. K. C. Nicolaou, S. P. Seitz, W. J. Sipio, and J. F. Blount, J. Am. Chem. Soc., 101, 3884 (1979).

    Google Scholar 

  77. R. V. Stevens and N. Hrib, Tetrahedron Lett., No. 48, 4791 (1981).

    Google Scholar 

  78. J. P. Marino and D. H. Floyd, J. Am. Chem. Soc., 96, 7138 (1974).

    Google Scholar 

  79. L.-C. Yu and P. Helquist, J. Org. Chem., 46, 4536 (1981).

    Google Scholar 

  80. W. C. Still and M. J. Schneider, J. Am. Chem. Soc., 99, 948 (1977).

    Google Scholar 

  81. S. Danishefsky, P. I. Schuda, T. Kitahara, and S. J. Etheredge, J. Am. Chem. Soc., 99, 6066 (1977).

    Google Scholar 

  82. D. M. Tschaen, E. Tyros, and S. M. Weinreb, J. Org. Chem., 49, 5058 (1984).

    Google Scholar 

  83. N. Petragnani and H. M. C. Ferraz, Synthesis, No. 6, 476 (1978).

    Google Scholar 

  84. S. Raucher, K.-J. Hwang, and J. E. Macdonald, Tetrahedron Lett., No. 33, 3057 (1979).

    Google Scholar 

  85. B. B. Snider and J. W. van Straten, J. Org. Chem., 44, 3567 (1979).

    Google Scholar 

  86. P. A. Bartlett and C. F. Pizzo, J. Org. Chem., 46, 3896 (1981).

    Google Scholar 

  87. P. A. Bartlett and J. F. Barstow, Tetrahedron Lett., No. 6, 623 (1982).

    Google Scholar 

  88. G. W. J. Fleet and C. R. C. Spensley, Tetrahedron Lett., No. 1, 109 (1982).

    Google Scholar 

  89. G. W. J. Fleet and M. J. Gough, Tetrahedron Lett., No. 43, 4509 (1982).

    Google Scholar 

  90. P. M. Cairus, C. Howes, P. R. Jenkins, D. R. Russell, and L. Sherry, Chem. Commun., No. 22, 1487 (1984).

    Google Scholar 

  91. E. J. Corey, M. Shibasaki, and J. Knolle, Tetrahedron Lett., No. 19, 1625 (1977).

    Google Scholar 

  92. R. R. Schmidt and W. Abele, Angew. Chem., 94, 298 (1982).

    Google Scholar 

  93. S. Ohuchida, N. Hamanaka, and M. Hayashi, Tetrahedron, 39, 4263 (1983).

    Google Scholar 

  94. B. Lythgoe, M. E. N. Nambudiry, and J. Tideswell, Tetrahedron Lett., No. 41, 3685 (1977).

    Google Scholar 

  95. H. O. House, R. G. Carlson, and H. Babad, J. Org. Chem., 28, 3359 (1963).

    Google Scholar 

  96. D. Johnson, J. W. Smart, and J. K. Sutherland, Chem. Commun., No. 14, 497 (1977).

    Google Scholar 

  97. A. J. Pearson, T. Ray, I. C. Richards, J. Clardy, and L. Silveira, Tetrahedron Lett., No. 52, 5827 (1983).

    Google Scholar 

  98. A. J. Pearson and T. Ray, Tetrahedron, 41, 5765 (1985).

    Google Scholar 

  99. J. A. Marschall and R. D. Royce, Jr., J. Org. Chem., 47, 693 (1982).

    Google Scholar 

  100. A. R. Chamberlin and S. H. Bloom, Tetrahedron Lett., No. 5, 551 (1986).

    Google Scholar 

  101. S. D. Burke, W. F. Fobare, and G. J. Pacofsky, J. Org. Chem., 48, 5221 (1983).

    Google Scholar 

  102. K. Mori and Y. Nakazono, Tetrahedron, 42, 283 (1986).

    Google Scholar 

  103. B. M. Trost, J. M. Timko, and J. L. Stanton, Chem. Commun., No. 10, 436 (1978).

    Google Scholar 

  104. D. J. Goldsmith and T. K. John, Synth. Commun., No. 7, 551 (1980).

    Google Scholar 

  105. K. C. Nicolaou and Z. Lysenko, J. Am. Chem. Soc., 99, 3185 (1977).

    Google Scholar 

  106. P. R. Brook and J. M. Harrison, Chem. Commun., No. 17, 997 (1972).

    Google Scholar 

  107. H. O. House, J. L. Haack, W. C. McDaniel, and D. Van Derveer, J. Org. Chem., 48, 1643 (1983).

    Google Scholar 

  108. S. Kobayashi, K. Kamiyama, T. Iimori, and M. Ohno, Tetrahedron Lett., No. 24, 2557 (1984).

    Google Scholar 

  109. D. Döpp, U. Langer, and H. Libera, Chem. Ber., 115, 346 (1982).

    Google Scholar 

  110. J. Meinwald, S. S. Labana, and M. S. Chadha, J. Am. Chem. Soc., 85, 582 (1963).

    Google Scholar 

  111. T. Uyehara, J. Yamada, K. Ogata, and T. Kato, Bull. Chem. Soc. Jpn., 58, 211 (1985).

    Google Scholar 

  112. F. Van Rantwijk, R. E. Van Der Stoel, and H. Van Bekkum, Recl. J. R. Neth. Chem. Soc., 100, 462 (1981).

    Google Scholar 

  113. G. Mass, Chem. Ber., 112, 3241 (1979).

    Google Scholar 

  114. B. A. Brown and E. W. Golvin, Chem. Commun., No. 22, 1514 (1984).

    Google Scholar 

  115. K. G. Bilyard and P. I. Garrat, Tetrahedron Lett., No. 18, 1755 (1981).

    Google Scholar 

  116. H. O. House, D. G. Melillo, and F. S. Sauter, J. Org. Chem., 38, 741 (1973).

    Google Scholar 

  117. S. Yamada, K. Hakayama, and H. Takayama, J. Org. Chem., 47, 4770 (1982).

    Google Scholar 

  118. G. W. Holbert, L. B. Weiss, and B. Ganem, Tetrahedron Lett., 49, 4435 (1976).

    Google Scholar 

  119. W. E. Barnett and L. L. Needham, J. Org. Chem., 40, 2843 (1975).

    Google Scholar 

  120. E. D. Brown, R. Clarkson, T. J. Leaney, and G. E. Robinson, Chem. Commun., No. 16, 642 (1974).

    Google Scholar 

  121. N. F. Bondar', T. N. Omel'chenko, and E. V. Koroleva, Zh. Org. Khim., 19, 1778 (1983).

    Google Scholar 

  122. E. J. Corey and H. E. Ensley, J. Am. Chem. Soc., 97, 6908 (1975).

    Google Scholar 

  123. E. J. Corey, H. E. Ensley, and J. W. Sugges, J. Org. Chem., 41, 380 (1976).

    Google Scholar 

  124. C. Gandolfi, G. Doria, and P. Gaio, Tetrahedron Lett., No. 42, 4303 (1972).

    Google Scholar 

  125. G. Doria, P. Gaio, and C. Gandolfi, Tetrahedron Lett., No. 42, 4307 (1972).

    Google Scholar 

  126. S. Ranganathan, D. Ranganathan, and A. K. Mehrotra, Tetrahedron Lett., No. 14, 1215 (1975).

    Google Scholar 

  127. P. Crabbe, A. Guzman, and E. Verlarde, Chem. Commun., No. 20, 1126 (1972).

    Google Scholar 

  128. E. J. Corey and G. Moinet, J. Am. Chem. Soc., 95, 6831 (1973).

    Google Scholar 

  129. E. D. Brown and T. J. Lilley, Chem. Commun., No. 1, 39 (1975).

    Google Scholar 

  130. P. A. Griego and T. Takigawa, J. Med. Chem., 24, 839 (1981).

    Google Scholar 

  131. P. R. Brook and J. M. Harrison, Chem. Commun., No. 17, 997 (1972).

    Google Scholar 

  132. P. R. Brook and K. Hunt, Chem. Commun., No. 23, 989 (1974).

    Google Scholar 

  133. R. C. De Selms and F. Delay, J. Org. Chem., 37, 2908 (1972).

    Google Scholar 

  134. K. Naemura and M. Nakasaki, Bull. Chem. Soc. Jpn., 46, 888 (1973).

    Google Scholar 

  135. M. L. Elliott, F. J. Urban, and J. Bordner, J. Org. Chem., 50, 1752 (1985).

    Google Scholar 

  136. C. A. Grob and P. Sawlewicz, Helv. Chim. Acta, 67, 1859 (1984).

    Google Scholar 

  137. S. Inokuma, A. Sugie, K. Moriguchi, H. Shimomura, and J. Katsube, Heterocycles, 19, 1419 (1982).

    Google Scholar 

  138. T. Poll, G. Helmchen, and B. Bayer, Tetrahedron Lett., No. 21, 2191 (1984).

    Google Scholar 

  139. R. M. Moriarty, C. C. Chien, and T. B. Adams, J. Org. Chem., 44, 2209 (1979).

    Google Scholar 

  140. é. G. Mamedov, I. M. Akhmedov, M. M. Guseinov, S. R. Piloyan, and E. I. Klabunovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 883 (1978).

    Google Scholar 

  141. W. Kirmse and K. Loosen, Chem. Ber., 114, 400 (1981).

    Google Scholar 

  142. é. B. Koryak, Yu. I. Gevaza, and V. I. Staninets, Ukr. Khim. Zh., 46, 178 (1980).

    Google Scholar 

  143. S. Masson and A. Thuillier, Bull. Soc. Chim. France, 10, 3508 (1971).

    Google Scholar 

  144. B. Giese and K. Heuck, Chem. Ber., 114, 1572 (1981).

    Google Scholar 

  145. D. Seyferth, J. Organomet. Chem., 41, 155 (1972).

    Google Scholar 

  146. A. McKillop, M. E. Ford, and E. C. Taylor, J. Org. Chem., 39, 2434 (1974).

    Google Scholar 

  147. S. Uemura, H. Miyoshi, and M. Okano, J. Organomet. Chem., 165, 9 (1979).

    Google Scholar 

  148. E. C. Taylor, G. E. Jagdmann, and A. McKillop, J. Org. Chem., 45, 3373 (1980).

    Google Scholar 

  149. K. C. Nicolaou and Z. Lysenko, Chem. Commun., No. 9, 293 (1977).

    Google Scholar 

  150. K. C. Nicolaou, W. J. Sipio, R. L. Magolda, and D. A. Claremon, Chem. Commun., No. 2, 83 (1979).

    Google Scholar 

  151. G. A. Tolstikov, V. M. Lerman, and N. G. Komissarova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1211 (1983).

    Google Scholar 

  152. J. P. Michael, N. F. Blom, and J. C. A. Boeyens, J. Chem. Soc., Perkin 1, No. 8, 1739 (1984).

    Google Scholar 

  153. I. Fleming, P. G. Jones, O. Kenuard, and J. P. Michael, J. Chem. Soc., Perkin 2, No. 6, 808 (1979).

    Google Scholar 

  154. I. Fleming and J. P. Michael, Chem. Commun., No. 6, 245 (1978).

    Google Scholar 

  155. I. Fleming and J. P. Michael, J. Chem. Soc., Perkin 1, No. 5, 1549 (1981).

    Google Scholar 

  156. K. Naemura and M. Nakasaki, Bull. Chem. Soc. Jpn., 46, 888 (1973).

    Google Scholar 

  157. D. J. Davies, H. D. Dowle, and R. F. Kenyon, Synthesis, No. 12, 990 (1979).

    Google Scholar 

  158. D. J. Davies and H. D. Dowle, J. Chem. Soc., Perkin 1, No. 21, 2267 (1976).

    Google Scholar 

  159. A. Bin Sedikyn and D. J. Davies, J. Chem. Soc., Perkin 1, No. 10, 2461 (1982).

    Google Scholar 

  160. A. Bin Sedikyn, D. J. Davies, S. N. Malek, and H. A. Bt, J. Chem. Soc., Perkin 2, No. 5, 703 (1983).

    Google Scholar 

  161. S. Ogawa, J. Kasahara, and T. Syami, Bull. Chem. Soc. Jpn., 52, 118 (1979).

    Google Scholar 

  162. S. Ogawa, Y. Iwasawa, and T. Syami, Chem. Lett., No. 3, 355 (1984).

    Google Scholar 

  163. S. Ogawa, Y. Iwasawa, T. Syami, S. Ohba, M. Ito, and Y. Saito, J. Chem. Soc., Perkin 1, No. 4, 903 (1985).

    Google Scholar 

  164. C. L. D. Jennings-White, A. B. Holmes, and P. R. Raithby, Chem. Commun., No. 12, 542 (1979).

    Google Scholar 

  165. M. M. Campbell, M. Sainsbury, and R. Javarzadeh, Tetrahedron, 40, 5063 (1984).

    Google Scholar 

  166. W. E. Barnett and W. H. Sohn, Chem. Commun., No. 8, 472 (1972).

    Google Scholar 

  167. W. E. Barnett and W. H. Sohn, Tetrahedron Lett., No. 18, 1777 (1972).

    Google Scholar 

  168. E. Crundwell and D. J. Mclntyre, Tetrahedron, 34, 1043 (1978).

    Google Scholar 

  169. T. Sasaki, K. Kanematsu, A. Kondo, and Y. Nishitani, J. Org. Chem., 39, 3569 (1974).

    Google Scholar 

  170. B. Giese, Chem. Ber., 108, 2998 (1975).

    Google Scholar 

  171. N. S. Zefirov, N. V. Zyk, S. I. Kolbasenko, and A. G. Kutateladze, J. Org. Chem., 50, 4539 (1985).

    Google Scholar 

  172. N. S. Zefirov, N. V. Zyk, A. G. Kutateladze, and Yu. A. Lapin, Zh. Org. Khim., 23, 392 (1987).

    Google Scholar 

  173. B. Giese and Ch. Daub, Chem. Ber., 110, 1101 (1977).

    Google Scholar 

  174. B. Giese, Chem. Ber., 107, 819 (1974).

    Google Scholar 

  175. B. Giese, Chem. Ber., 108, 2978 (1975).

    Google Scholar 

  176. S. Ranganathan, D. Ranganathan, and A. K. Mehrotra, Tetrahedron, 33, 807 (1977).

    Google Scholar 

  177. D. Bellus, K. Bredow, H. Sauter, and C. D. Weis, Helv. Chim. Acta, 56, 3004 (1973).

    Google Scholar 

  178. D. G. Garrat, M. D. Ryan, and P. L. Beaulieu, J. Org. Chem., 45, 839 (1980).

    Google Scholar 

  179. I. Fleming, J. P. Michael, L. E. Overman, and G. F. Taylor, Tetrahedron Lett., No. 15, 1313 (1978).

    Google Scholar 

  180. N. P. Shusherina and N. V. Gapeeva, Zh. Org. Khim., 9, 1190 (1973).

    Google Scholar 

  181. T. Sasaki, K. Kanematsu, A. Korido, and Y. Nischitani, J. Org. Chem., 39, 3569 (1974).

    Google Scholar 

  182. L. A. Paquette, H. C. Berk, C. R. Degenhardt, and G. D. Ewing, J. Am. Chem. Soc., 99, 4764 (1977).

    Google Scholar 

  183. T. Sasaki, K. Kanematsu, and A. Kondo, J. Org. Chem., 39, 2246 (1974).

    Google Scholar 

  184. G. Mehta, P. K. Dutta, and P. N. Pandey, Tetrahedron Lett., No. 7, 445 (1975).

    Google Scholar 

  185. G. Mehta and P. N. Pandey, J. Org. Chem., 40, 3631 (1975).

    Google Scholar 

  186. C. J. Fray, R. Geen, D. I. Davies, L. T. Parfitt, and M. J. Parrott, J. Chem. Soc., Perkin 1, No. 7, 729 (1974).

    Google Scholar 

  187. T. Sasaki, K. Kanematsu, and A. Kondo, J. Org. Chem., 40, 1542 (1975).

    Google Scholar 

  188. N. S. Zefirov, N. K. Sadovaya, V. N. Kirin, A. S. Koz'min, and I. V. Bodrikov, Zh. Org. Khim., 13, 228 (1977).

    Google Scholar 

  189. T. Sasaki, K. Kanematsu, and A. Kondo, J. Chem. Soc., Perkin 1, No. 23, 2516 (1976).

    Google Scholar 

  190. T. Sasaki, K. Kanematsu, A. Kondo, and K. Okada, J. Org. Chem., 41, 2231 (1976).

    Google Scholar 

  191. T. Sasaki, K. Kanematsu, and A. Kondo, Tetrahedron, 31, 2215 (1975).

    Google Scholar 

  192. N. S. Zefirov, V. N. Kirin, A. S. Koz'min (Kozmin), I. V. Bodrikov, K. A. Potekhin, and E. N. Kurkutova, Tetrahedron Lett., No. 29, 2617 (1978).

    Google Scholar 

  193. K. A. Potekhin, E. N. Kurkutova, Yu. T. Struchkov, V. N. Kirin, A. S. Koz'min, N. S. Zefirov, V. V. Ilyukhin, and N. V. Belov, Dokl. Akad. Nauk SSSR, 243, 348 (1978).

    Google Scholar 

  194. A. Kondo, T. Yamane, T. Ashida, T. Sasaki, and K. Kanematsu, J. Org. Chem., 43, 1180 (1978).

    Google Scholar 

  195. N. S. Zefirov, V. N. Kirin, A. S. Kuz'min, and M. Z. Krimer, Zh. Org. Khim., 17, 13 (1981).

    Google Scholar 

  196. N. S. Zefirov, V. N. Kirin, K. A. Potekhin, A. S. Koz'min, N. K. Sadovaya, E. N. Kurkutova, and I. V. Bodrikov, Zh. Org. Khim., 14, 1224 (1978).

    Google Scholar 

  197. N. S. Zefirov, A. S. Koz'min (Kozmin), V. N. Kirin, V. V. Zhdankin, G. V. Lagodzinskaya, K. A. Potekhin, and E. N. Kurkutova, Nouv. J. Chim., 4, 475 (1980).

    Google Scholar 

  198. N. S. Zefirov, A. S. Koz'min (Kozmin), V. V. Zhdankin, V. N. Kirin, I. V. Bodrikov, B. Sedov, and V. G. Rau, Tetrahedron Lett., No. 37, 3533 (1979).

    Google Scholar 

  199. N. V. Zyk, L. V. Nikulin, S. I. Kolbasenko, A. G. Kutateladze, and N. S. Zefirov, Zh. Org. Khim., 20, 1329 (1984).

    Google Scholar 

  200. N. S. Zefirov, A. S. Koz'min (Kozmin), and V. V. Zhdankin, Tetrahedron, 38, 291 (1982).

    Google Scholar 

  201. N. S. Zefirov, A. S. Koz'min (Kozmin), V. V. Zhdankin, A. V. Nikulin, and N. V. Zyk. J. Org. Chem., 47, 3679 (1982).

    Google Scholar 

  202. D. G. Garratt, M. D. Ryan, and A. Kabo, Can. J. Chem., 58, 2329 (1980).

    Google Scholar 

  203. M. MühlstÄdt and R. Widera, J. prakt. Chem., 372, 139 (1980).

    Google Scholar 

  204. M. MühlstÄdt, B. Olk, and R. Widera, Tetrahedron Lett., No. 37, 3979 (1983).

    Google Scholar 

  205. S. Knapp and D. V. Patel, Tetrahedron Lett., 23, 3539 (1982).

    Google Scholar 

  206. S. Takano and S. Hatakeyama, Heterocycles, 19, 1243 (1982).

    Google Scholar 

  207. S. Knapp and D. V. Patel, J. Org. Chem., 49, 5072 (1984).

    Google Scholar 

  208. S. Kobayashi, T. Isobe, and M. Ohno, Tetrahedron Lett., No. 44, 5079 (1984).

    Google Scholar 

  209. H. W. Pauls and B. Fraser-Reid, J. Am. Chem. Soc., 102, 3956 (1980).

    Google Scholar 

  210. M. Georges and B. Fraser-Reid, Tetrahedron Lett., No. 46, 4635 (1981).

    Google Scholar 

  211. M. Hirama, M. Iwashita, Y. Yamazaki, and S. Ito, Tetrahedron Lett., No. 43, 4963 (1984).

    Google Scholar 

  212. S.-S. Jew, S. Terashima, and K. Koga, Tetrahedron, 35, 2337 (1979).

    Google Scholar 

  213. M. Hayashi, S. Teraahima, and K. Koga, Tetrahedron, 37, 2797 (1981).

    Google Scholar 

  214. S. Terashima, M. Hayashi, and K. Koga, Tetrahedron Lett., 21, 2733 (1980).

    Google Scholar 

  215. T. Kitazune, T. Sato, T. Kobayoshi, and J. Lin, J. Org. Chem., 51, 1003 (1986).

    Google Scholar 

  216. K. A. Parker and R. O'Fee, J. Am. Chem. Soc., 105, 654 (1983).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Academy of Sciences of the Ukrainian SSR, 252660, Kiev

    Yu. I. Gevaza & V. I. Staninets

Authors
  1. Yu. I. Gevaza
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. I. Staninets
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1299–1316, October, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gevaza, Y.I., Staninets, V.I. Electrophilic heterocyclization of unsaturated carboxylic acids in the synthesis of lactones (review). Chem Heterocycl Compd 24, 1073–1088 (1988). https://doi.org/10.1007/BF00475678

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00475678

Keywords

Search

Navigation