Skip to main content

Formation of Cyclic Structures

  • Chapter
Elements of Synthesis Planning
  • 2147 Accesses

Abstract

Rings in a target structure are to be made from acyclic precursors by intramolecular one-bond formation (ring closure reaction) or by two-bond formation in a cycloaddition reaction. Bicyclic and polycyclic target structures are approached in the same way, whereby two-bond disconnections or multi-bond disconnections in reaction cascades are preferred. Multi-bond disconnections may be advantageous, even when a surplus extra bond is generated in the forward synthesis.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 49.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 64.99
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. C. P. Dell, J. Chem. Soc., Perkin Trans. 1, 1998, 3873–3905.

    Google Scholar 

  2. P. A. Wender, J. A. Love, Advances in Cycloaddition 1999, 5, 1–45.

    CAS  Google Scholar 

  3. S. H. Bertz, New J. Chem. 2003, 27, 860–869.

    CAS  Google Scholar 

  4. G. Büchi, H. Wüest, Helv. Chim. Acta 1971, 54, 1767–1776.

    Google Scholar 

  5. M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49–92.

    CAS  Google Scholar 

  6. S. J. Hedley, W. J. Moran, D. A. Price, J. P. A. Harrity, J. Org. Chem. 2003, 68, 4286–4292.

    CAS  Google Scholar 

  7. W. J. Moran, K. M. Goodenough, P. Raubo, J. P. A. Harrity, Org. Lett. 2003, 5, 3427–3429.

    CAS  Google Scholar 

  8. A. V. Kurdyumov, R. P. Hsung, K. Ihlen, J. Wang, Org. Lett. 2003, 5, 3935–3938.

    CAS  Google Scholar 

  9. J. P. A. Harrity, O. Provoost, Org. Biomol. Chem. 2005, 3, 1349–1358.

    CAS  Google Scholar 

  10. A. I. Gerasyuto, R. P. Hsung, N. Sydorenko, B. Slafer, J. Org. Chem. 2005, 70, 4248–4256.

    CAS  Google Scholar 

  11. R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 6330–6331.

    CAS  Google Scholar 

  12. J. Sauer, R. Sustmann, Angew. Chem., Int. Ed. Engl. 1980, 19, 779–807. (Angew. Chem. 1980, 92, 773–801).

    Google Scholar 

  13. A. Hosomi, M. Saito, H. Sakurai, Tetrahedron Lett. 1980, 21, 355–358.

    CAS  Google Scholar 

  14. S. J. Danishefsky, Acc. Chem. Res. 1981, 14, 400–406.

    CAS  Google Scholar 

  15. J. Sauer, Angew. Chem., Int. Ed. Engl. 1967, 6, 16–33. (Angew. Chem. 1967, 79, 76–94).

    CAS  Google Scholar 

  16. P. G. Gassman, D. A. Singleton, J. J. Wilwerding, S. P. Chavan, J. Am. Chem. Soc. 1987, 109, 2182–2184.

    CAS  Google Scholar 

  17. P. G. Gassman, S. P. Chavan, Tetrahedron Lett. 1988, 29, 3407–3410.

    CAS  Google Scholar 

  18. M. Harmata, P. Rashatasakhon, Tetrahedron 2003, 59, 2371–2395.

    CAS  Google Scholar 

  19. B. M. Trost, J. Ippen, W. C. Vladuchick, J. Am. Chem. Soc. 1977, 99, 8116–8118.

    CAS  Google Scholar 

  20. B. M. Trost, W. C. Vladuchick, A. J. Bridges, J. Am. Chem. Soc. 1980, 102, 3554–3572.

    CAS  Google Scholar 

  21. P. Kozikowski, E. M. Huie, J. Am. Chem. Soc. 1982, 104, 2923–2925.

    CAS  Google Scholar 

  22. P. J. Proteau, P. B. Hopkins, J. Org. Chem. 1985, 50, 141–143.

    CAS  Google Scholar 

  23. P. V. Alston, M. D. Gordon, R. M. Ottenbrite, T. Cohen, J. Org. Chem. 1983, 48, 5051–5054.

    CAS  Google Scholar 

  24. D. A. Singleton, J. P. Martinez, J. Am. Chem. Soc. 1990, 112, 7423–7424.

    CAS  Google Scholar 

  25. D. A. Singleton, S.-W. Leung, J. Org. Chem. 1992, 57, 4796–4797.

    CAS  Google Scholar 

  26. S. Danishefsky, M. P. Prisbylla, S. Hiner, J. Am. Chem. Soc. 1978, 100, 2918–2920.

    CAS  Google Scholar 

  27. G. Stork, P. C. Tang, M. Casey, B. Goodman, M. Toyota, J. Am. Chem. Soc. 2005, 127, 16255–16262.

    CAS  Google Scholar 

  28. R. V. C. Carr, L. A. Paquette, J. Am. Chem. Soc. 1980, 102, 853–855.

    CAS  Google Scholar 

  29. O. DeLucchi, G. Modena, Tetrahedron 1984, 40, 2585–2632.

    CAS  Google Scholar 

  30. N. Ono, A. Kamimura, A. Kaji, J. Org. Chem. 1988, 53, 251–258.

    CAS  Google Scholar 

  31. A. C. Brown, L. A. Carpino, J. Org. Chem. 1985, 50, 1749–1750.

    CAS  Google Scholar 

  32. R. N. Warrener, R. A. Russel, R. Solomon, I. G. Pitt, D. N. Butler, Tetrahedron Lett. 1987, 28, 6503–6506.

    CAS  Google Scholar 

  33. G. Hilt, T. J. Korn, Tetrahedron Lett. 2001, 42, 2783–2785.

    CAS  Google Scholar 

  34. G. Hilt, K. I. Smolko, B. V. Lotsch, Synlett 2002, 1081–1084.

    Google Scholar 

  35. S. Ranganathan, D. Ranganathan, A. K. Mehrotra, Synthesis 1977, 289–296.

    Google Scholar 

  36. R. V. Williams, X. Lin, J. Chem. Soc., Chem. Commun. 1989, 1872–1873.

    Google Scholar 

  37. V. K. Aggarwal, Z. Gültekin, R. S. Grainger, H. Adams, P. L. Spargo, J. Chem. Soc., Perkin Trans. 1, 1998, 2771–2781.

    Google Scholar 

  38. W. G. Dauben, H. O. Krabbenhoft, J. Org. Chem. 1977, 42, 282–287.

    CAS  Google Scholar 

  39. R. W. Rickards, H. Rönneberg, J. Org. Chem. 1984, 49, 572–573.

    CAS  Google Scholar 

  40. G. M. Sammis, E. M. Flamme, H. Xie, D. M. Ho, E. J. Sorensen, J. Am. Chem. Soc. 2005, 127, 8612–8613.

    CAS  Google Scholar 

  41. M. J. Carter, I. Fleming, A. Percival, J. Chem. Soc., Perkin Trans. 1, 1981, 2415–2434.

    Google Scholar 

  42. D. A. Evans, C. A. Bryan, C. L. Sims, J. Am. Chem. Soc. 1972, 94, 2891–2892.

    CAS  Google Scholar 

  43. E. Arce, M. C. Carreno, M. B. Cid, J. L. Garcia Ruano, J. Org. Chem. 1994, 59, 3421–3426.

    CAS  Google Scholar 

  44. E. J. Kantorowski, M. J. Kurth, Tetrahedron 2000, 56, 4317–4353.

    CAS  Google Scholar 

  45. Y. Mori, K. Yaegashi, T. Furukawa, Tetrahedron 1997, 53, 12917–12932.

    CAS  Google Scholar 

  46. J. W. Cornforth, R. Robinson, J. Chem. Soc. 1949, 1855–1865.

    Google Scholar 

  47. M. Ramaiah, Synthesis 1984, 529–570.

    Google Scholar 

  48. L. A. Paquette, Topics Curr. Chem. 1984, 119, 2–12.

    Google Scholar 

  49. M. Vandewalle, P. De Clercq, Tetrahedron 1985, 41, 1767–1831.

    CAS  Google Scholar 

  50. G. Büchi, M. Pawlack, J. Org. Chem. 1975, 40, 100–102.

    Google Scholar 

  51. K. G. Bilyard, P. J. Garratt, A. J. Underwood, R. Zahler, Tetrahedron Lett. 1979, 20, 1815–1818.

    Google Scholar 

  52. J. E. McMurry, D. D. Miller, J. Am. Chem. Soc. 1983, 105, 1660–1661.

    CAS  Google Scholar 

  53. M. E. Garst, B. J. McBride, A. T. Johnson, J. Org. Chem. 1983, 48, 8–16.

    CAS  Google Scholar 

  54. P. Wasnaire, T. de Merode, I. E. Markó, Chem. Commun. 2007, 4755–4757.

    Google Scholar 

  55. R. J. Pariza, P. L. Fuchs, J. Org. Chem. 1983, 48, 2304–2306.

    CAS  Google Scholar 

  56. S. E. Denmark, J. P. Germanas, Tetrahedron Lett. 1984, 25, 1231–1234.

    CAS  Google Scholar 

  57. E. J. Corey, D. L. Boger, Tetrahedron Lett. 1978, 19, 2461–2464.

    Google Scholar 

  58. K. E. Harding, P. M. Puckett, J. L. Cooper, Bioorg. Chem 1978, 7, 221–234.

    CAS  Google Scholar 

  59. J. A. Thomas, C. H. Heathcock, Tetrahedron Lett. 1980, 21, 3235–3236.

    CAS  Google Scholar 

  60. W. P. Jackson, S. V. Ley, A. J. Whittle, J. Chem. Soc., Chem. Commun. 1980, 1173–1174.

    Google Scholar 

  61. F. Näf, R. Decorzant, W. Thommen, Helv. Chim. Acta 1975, 58, 1808–1812.

    Google Scholar 

  62. J. M. Conia, G. Moinet, Bull. Soc. Chim Fr. 1969, 500–508.

    Google Scholar 

  63. P. T. Lansbury, N. Nazarenko, Tetrahedron Lett. 1971, 12, 1833–1836.

    Google Scholar 

  64. Y. Hayakawa, K. Yokoyama, R. Noyori, J. Am. Chem. Soc. 1978, 100, 1799–1806.

    CAS  Google Scholar 

  65. B. M. Trost, D. P. Curran, J. Am. Chem. Soc. 1980, 102, 5699–5700.

    CAS  Google Scholar 

  66. H. J. Altenbach, Angew. Chem., Int. Ed. Engl. 1979, 18, 940–941. (Angew. Chem. 1979, 91, 1005–1006).

    Google Scholar 

  67. W. G. Dauben, D. J. Hart, J. Org. Chem. 1977, 42, 3787–3793.

    CAS  Google Scholar 

  68. G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz, R. Terrell, J. Am. Chem. Soc. 1963, 85, 207–222.

    CAS  Google Scholar 

  69. E. Piers, B. Abeysekera, J. R. Scheffer, Tetrahedron Lett. 1979, 20, 3279–3282.

    Google Scholar 

  70. M. Miyashita, T. Yanami, A. Yoshikoshi, J. Am. Chem. Soc. 1976, 98, 4679–4681.

    CAS  Google Scholar 

  71. P. T. Lansbury, E. J. Nienhouse, J. Am. Chem. Soc. 1966, 88, 4290–4291.

    CAS  Google Scholar 

  72. J. R. Matz, T. Cohen, Tetrahedron Lett. 1981, 22, 2459–2462.

    CAS  Google Scholar 

  73. M. Karpf, A. S. Dreiding, Helv. Chim. Acta 1979, 62, 852–865.

    CAS  Google Scholar 

  74. B. M. Trost, Acc. Chem. Res. 1974, 7, 85–92.

    CAS  Google Scholar 

  75. G. Stork, N. H. Baine, J. Am. Chem. Soc. 1982, 104, 2321–2323.

    CAS  Google Scholar 

  76. X. Shi, D. J. Gorin, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 5802–5803.

    CAS  Google Scholar 

  77. A. Murfat, P. Helquist, Tetrahedron Lett. 1978, 19, 4217–4220.

    Google Scholar 

  78. W. C. Agosta, S. Wolff, J. Org. Chem. 1975, 40, 1699–1701.

    CAS  Google Scholar 

  79. E. Piers, C. K. Lau, I. Nagakura, Tetrahedron Lett. 1976, 17, 3233–3236.

    Google Scholar 

  80. S. Knapp, U. O’Connor, D. Mobilio, Tetrahedron Lett. 1980, 21, 4557–4560.

    CAS  Google Scholar 

  81. R. L. Danheiser, D. J. Carini, D. M. Fink, A. Basak, Tetrahedron 1983, 39, 935–947.

    CAS  Google Scholar 

  82. T. Hiyama, M. Shinoda, H. Nozaki, Tetrahedron Lett. 1978, 19, 771–774.

    Google Scholar 

  83. H. Stetter, I. Krüger-Hansen, M. Rizk, Chem. Ber. 1961, 94, 2702–2707.

    CAS  Google Scholar 

  84. E. Piers, V. Karunaratne, J. Chem. Soc., Chem. Commun. 1983, 935–936.

    Google Scholar 

  85. N. N. Marinovic, H. Ramanathan, Tetrahedron Lett. 1983, 24, 1871–1874.

    CAS  Google Scholar 

  86. G. Majetich, R. Desmond, A. M. Casares, Tetrahedron Lett. 1983, 24, 1913–1916.

    CAS  Google Scholar 

  87. S. Danishefsky, S. Chackalamannil, B.-J. Uang, J. Org. Chem. 1982, 47, 2231–2232.

    CAS  Google Scholar 

  88. T. Shono, I. Nishiguchi, H. Omizu, Chem. Lett. 1976, 5, 1233–1236.

    Google Scholar 

  89. E. J. Corey, M. A. Tius, J. Das, J. Am. Chem. Soc. 1980, 102, 1742–1744.

    CAS  Google Scholar 

  90. J. Justicia, J. E. Oltra, J. M. Cuerva, J. Org. Chem. 2005, 70, 8265–8272.

    CAS  Google Scholar 

  91. J. Dijkink, W. N. Speckamp, Tetrahedron Lett. 1977, 18, 935–938.

    Google Scholar 

  92. D. Nasipuri, G. Das, J. Chem. Soc., Perkin Trans. 1, 1979, 2776–2778.

    Google Scholar 

  93. T. Hudlicky, F. J. Koszyk, D. M. Dochwat, G. L. Cantrell, J. Org. Chem. 1981, 46, 2911–2915.

    CAS  Google Scholar 

  94. W. R. Roush, H. R. Gillis, A. I. Ko, J. Am. Chem. Soc. 1982, 104, 2269–2283.

    CAS  Google Scholar 

  95. E. Ciganek, Org. Reactions 1984, 32, 1–374.

    CAS  Google Scholar 

  96. D. Craig, Chem. Soc. Rev. 1987, 16, 187–238.

    CAS  Google Scholar 

  97. W. Oppolzer, Angew. Chem., Int. Ed. Engl. 1977, 16, 10–23. (Angew. Chem. 1977, 89, 10–24).

    Google Scholar 

  98. G. Brieger, J. N. Bennett, Chem. Rev. 1980, 80, 63–97.

    CAS  Google Scholar 

  99. M. E. Jung, K. M. Halweg, Tetrahedron Lett. 1981, 22, 2735–2738.

    CAS  Google Scholar 

  100. W. Oppolzer, W. Fröstl, H. P. Weber, Helv. Chim. Acta 1975, 58, 593–595.

    CAS  Google Scholar 

  101. M. Braun, Nachr. Chem. Techn. Lab. 1985, 33, 718–725.

    CAS  Google Scholar 

  102. N.-Y. Wang, C.-T. Hsu, C. J. Sih, J. Am. Chem. Soc. 1981, 103, 6538–6539.

    CAS  Google Scholar 

  103. N. N. Girotra, N. L. Wendler, Tetrahedron Lett. 1983, 24, 3687–3688.

    CAS  Google Scholar 

  104. P. A. Grieco, R. E. Zelle, R. Lis, J. Finn, J. Am. Chem. Soc. 1983, 105, 1403–1404.

    CAS  Google Scholar 

  105. S. J. Danishefsky, B. Simoneau, J. Am. Chem. Soc. 1989, 111, 2599–2604.

    CAS  Google Scholar 

  106. C. H. Heathcock, M. J. Taschner, T. Rosen, J. A. Tomas, C. R. Hadley, G. Popjak, Tetrahedron Lett. 1982, 23, 4747–4750.

    CAS  Google Scholar 

  107. P. M. Wovkulich, P. C. Tang, N. K. Chadha, A. D. Batcho, J. C. Barrish, M. R. Uskokovic, J. Am. Chem. Soc. 1989, 111, 2596–2599.

    CAS  Google Scholar 

  108. P. C. Anderson, D. L. J. Clive, C. F. Evans, Tetrahedron Lett. 1983, 24, 1373–1376.

    CAS  Google Scholar 

  109. R. L. Funk, C. J. Mossman, W. E. Zeller, Tetrahedron Lett. 1984, 25, 1655–1658.

    CAS  Google Scholar 

  110. M. Hirama, M. Uei, J. Am. Chem. Soc. 1982, 104, 4251–4253.

    CAS  Google Scholar 

  111. R. L. Funk, W. E. Zeller, J. Org. Chem. 1982, 47, 180–182.

    CAS  Google Scholar 

  112. E. A. Deutsch, B. B. Snider, J. Org. Chem. 1982, 47, 2682–2684.

    CAS  Google Scholar 

  113. G. E. Keck, D. F. Kachensky, J. Org. Chem. 1986, 51, 2487–2493.

    CAS  Google Scholar 

  114. Y.-L. Yang, S. Manna, J. R. Falck, J. Am. Chem. Soc. 1984, 106, 3811–3814.

    CAS  Google Scholar 

  115. J. R. Falck, Y.-L. Yang, Tetrahedron Lett. 1984, 25, 3563–3566.

    CAS  Google Scholar 

  116. T. Sammakia, D. M. Johns, G. Kim, M. A. Berliner, J. Am. Chem. Soc. 2005, 127, 6504–6505.

    CAS  Google Scholar 

  117. H. Muxfeldt, W. Rogalski, J. Am. Chem. Soc. 1965, 87, 933–934.

    CAS  Google Scholar 

  118. J. J. Korst, J. D. Johnston, K. Butler, E. J. Bianco, L. H. Conover, R. B. Woodward, J. Am. Chem. Soc. 1968, 90, 439–457.

    CAS  Google Scholar 

  119. K. Maruyama, H. Uno, Y. Naruta, Chem. Lett. 1983, 12, 1767–1770.

    Google Scholar 

  120. G. A. Kraus, S. H. Woo, J. Org. Chem. 1987, 52, 4841–4846.

    CAS  Google Scholar 

  121. Y. Naruta, Y. Nishigaichi, K. Maruyama, J. Org. Chem. 1988, 53, 1192–1199.

    CAS  Google Scholar 

  122. T. Kametani, H. Nemoto, H. Ishikawa, K. Shiroyama, H. Matsumoto, K Fukumoto, J. Am. Chem. Soc. 1977, 99, 3461–3466.

    CAS  Google Scholar 

  123. W. Oppolzer, K. Bättig, M. Petrzilka, Helv. Chim. Acta 1978, 61, 1945–1947.

    CAS  Google Scholar 

  124. W. Oppolzer, D. A. Roberts, Helv. Chim. Acta 1980, 63, 1703–1705.

    CAS  Google Scholar 

  125. K. C. Nicolaou, W. E. Barnette, P. Ma, J. Org. Chem. 1980, 45, 1463–1470.

    CAS  Google Scholar 

  126. G. Quinkert, U. Schwartz, H. Stark, W.-D. Weber, H. Baier, F. Adam, G. Dürner, Angew. Chem., Int. Ed. Engl. 1980, 19, 1029–1030. (Angew. Chem. 1980, 92, 1062–1063).

    Google Scholar 

  127. R. L. Funk, K. P. C. Vollhardt, J. Am. Chem. Soc. 1977, 99, 5483–5484.

    CAS  Google Scholar 

  128. E. J. Corey, W. J. Howe, H. W. Orf, D. A. Pensak, G. Petersson, J. Am. Chem. Soc. 1975, 97, 6116–6124.

    CAS  Google Scholar 

  129. B. Lei, A. G. Fallis, J. Org. Chem. 1993, 58, 2186–2195.

    CAS  Google Scholar 

  130. B. B. Snider, H. Lin, J. Am. Chem. Soc. 1999, 121, 7778–7786.

    CAS  Google Scholar 

  131. G. Scheffler, H. Seike, E. J. Sorensen, Angew. Chem., Int. Ed. 2000, 39, 4593–4596. (Angew. Chem. 2000, 112, 4783–4785).

    CAS  Google Scholar 

  132. M. Ousmer, N. A. Braun, M. A. Ciufolini, Org. Lett. 2001, 3, 765–767.

    CAS  Google Scholar 

  133. J.-H. Maeng, R. L. Funk, Org. Lett. 2001, 3, 1125–1128.

    CAS  Google Scholar 

  134. D. J. Wardrop, W. Zhang, Org. Lett. 2001, 3, 2353–2356.

    CAS  Google Scholar 

  135. K. M. Brummond, J. Lu, Org. Lett. 2001, 3, 1347–1349.

    CAS  Google Scholar 

  136. J. Sisko, J. R. Henry, S. M. Weinreb, J. Org. Chem. 1993, 58, 4945–4951.

    CAS  Google Scholar 

  137. S. Hong, J. Yang, S. M. Weinreb, J. Org. Chem. 2006, 71, 2078–2089.

    CAS  Google Scholar 

  138. C. S. Ge, S. Hourcade, A. Ferdenzi, A. Chiaroni, S. Mons, B. Delpech, C. Marazano, Eur. J. Org. Chem. 2006, 4106–4114.

    Google Scholar 

  139. R. Downham, F. W. Ng, L. E. Overman, J. Org. Chem. 1998, 63, 8096–8097.

    CAS  Google Scholar 

  140. C. J. Douglas, S. Hiebert, L. E. Overman, Org. Lett. 2005, 7, 933–936.

    CAS  Google Scholar 

  141. D. J. Denhart, D. A. Griffith, C. H. Heathcock, J. Org. Chem. 1998, 63, 9616–9617.

    CAS  Google Scholar 

  142. M. E. Maier, Nachr. Chem. Tech. Lab. 1993, 41, 1120–1128.

    CAS  Google Scholar 

  143. D. A. Evans, C. H. Mitch, Tetrahedron Lett. 1982, 23, 285–288.

    CAS  Google Scholar 

  144. K. A. Parker, D. Fokas, J. Am. Chem. Soc. 1992, 114, 9688–9689.

    CAS  Google Scholar 

  145. K. A. Parker, D. Fokas, J. Org. Chem. 2006, 71, 449–455.

    CAS  Google Scholar 

  146. B. M. Trost, W. Tang, F. Dean Toste, J. Am. Chem. Soc. 2005, 127, 14785–14803.

    CAS  Google Scholar 

  147. C. Y. Hong, N. Kado, L. E. Overman, J. Am. Chem. Soc. 1993, 115, 11028–11029.

    CAS  Google Scholar 

  148. C. Y. Hong, L. E. Overman, Tetrahedron Lett. 1994, 35, 3453–3456.

    CAS  Google Scholar 

  149. D. Trauner, J. W. Bats, A. Werner, J. Mulzer, J. Org. Chem. 1998, 63, 5908–5918.

    CAS  Google Scholar 

  150. S. D. Burke, C. W. Murtiashaw, J. O. Saunders, J. A. Oplinger, M. S. Dike, J. Am. Chem. Soc. 1984, 106, 4558–4566.

    CAS  Google Scholar 

  151. S. Kim, D. H. Oh, J.-Y. Yoon, J. H. Cheong, J. Am. Chem. Soc. 1999, 121, 5330–5331.

    CAS  Google Scholar 

  152. A. B. Smith III, B. A. Wexler, J. Slade, Tetrahedron Lett. 1982, 23, 1631–1634.

    CAS  Google Scholar 

  153. A. S. Kende, B. Roth, P. J. Sanfilippo, T. J. Blacklock, J. Am. Chem. Soc. 1982, 104, 5808–5810.

    CAS  Google Scholar 

  154. S. Danishefsky, K. Vaughan, R. Gadwood, K. Tsuzuki, J. Am. Chem. Soc. 1981, 103, 4136–4141.

    CAS  Google Scholar 

  155. W. K. Bornack, S. S. Bhagwat, J. Ponton, P. Helquist, J. Am. Chem. Soc. 1981, 103, 4647–4648.

    CAS  Google Scholar 

  156. K. Kon, K. Ito, S. Isoe, Tetrahedron Lett. 1984, 25, 3739–3742.

    CAS  Google Scholar 

  157. A. P. Neary, P. J. Parsons, J. Chem. Soc., Chem. Commun. 1989, 1090–1091.

    Google Scholar 

  158. R. H. Schlessinger, J. L. Wood, A. J. Poss, R. A. Nugent, W. H. Parsons, J. Org. Chem. 1983, 48, 1146–1147.

    CAS  Google Scholar 

  159. J. M. Dewanckele, F. Zutterman, M. Vandewalle, Tetrahedron 1983, 39, 3235–3244.

    CAS  Google Scholar 

  160. E. Piers, N. Moss, Tetrahedron Lett. 1985, 26, 2735–2738.

    CAS  Google Scholar 

  161. H.-J. Liu, M. Llinas-Brunet, Can. J. Chem. 1988, 66, 528–530.

    CAS  Google Scholar 

  162. C. H. Heathcock, Angew. Chem., Int. Ed. Engl. 1992, 31, 665–681. (Angew. Chem. 1992, 104, 675–691).

    Google Scholar 

  163. G. Büchi, W. D. MacLeod Jr., J. Am. Chem. Soc. 1962, 84, 3205–3206.

    Google Scholar 

  164. M. Dobler, J. D. Dunitz, B. Gubler, H. P. Weber, G. Büchi, O. J. Padilla, Proc. Chem. Soc. (London) 1963, 383.

    Google Scholar 

  165. E. J. Corey, W. T. Wipke, Science 1969, 166, 178–192.

    CAS  Google Scholar 

  166. F. Näf, R. Decorzant, W. Giersch, G. Ohloff, Helv. Chim. Acta 1981, 64, 1387–1397.

    Google Scholar 

  167. J. B. Hendrickson, J. Am. Chem. Soc. 1986, 108, 6748–6756.

    CAS  Google Scholar 

  168. P. A. Wender, D. J. Wolanin, J. Org. Chem. 1985, 50, 4418–4420.

    CAS  Google Scholar 

  169. A. B. Smith III, J. P. Konopelski, B. A. Wexler, P. A. Spengeler, J. Am. Chem. Soc. 1991, 113, 3533–3542.

    CAS  Google Scholar 

  170. R. L. Funk, M. M. Abelman, J. Org. Chem. 1986, 51, 3247–3248.

    CAS  Google Scholar 

  171. P. A. Wender, Selectivity – a Goal for Synthetic Efficiency (Eds.: W. Bartmann, B. M. Trost), Verlag Chemie, Weinheim, 1984, pp. 335–348.

    Google Scholar 

  172. T. Imanishi, M. Matsui, M. Yamashita, C. Iwata, Tetrahedron Lett. 1986, 27, 3161–3164.

    CAS  Google Scholar 

  173. T. Imanishi, M. Matsui, M. Yamashita, C. Iwata, J. Chem. Soc., Chem. Commun. 1987, 1802–1804.

    Google Scholar 

  174. D. Caine, W. R. Pennington, T. L. Smith jr, Tetrahedron Lett. 1978, 2663–2666.

    Google Scholar 

  175. J. F. Ruppert, J. D. White, J. Am. Chem. Soc. 1981, 103, 1808–1813.

    CAS  Google Scholar 

  176. W. Oppolzer, T. Godel, J. Am. Chem. Soc. 1978, 100, 2583–2584.

    CAS  Google Scholar 

  177. R. M. Coates, J. W. Muskopf, P. A. Senter, J. Org. Chem. 1985, 50, 3541–3557.

    CAS  Google Scholar 

  178. C. M. Amann, P. V. Fisher, M. L. Pugh, F. G. West, J. Org. Chem. 1998, 63, 2806–2807.

    CAS  Google Scholar 

  179. A. Hosomi, Y. Matsuyama, H. Sakurai, J. Chem. Soc., Chem. Commun. 1986, 1073–1074.

    Google Scholar 

  180. B. A. Pearlman, J. Am. Chem. Soc. 1979, 101, 6398–6404.

    CAS  Google Scholar 

  181. P. A. Wender, J. C. Lechleiter, J. Am. Chem. Soc. 1977, 99, 267–268.

    CAS  Google Scholar 

  182. W. Oppolzer, Acc. Chem. Res. 1982, 15, 135–141.

    CAS  Google Scholar 

  183. D. Becker, Z. Harel, M. Nagler, A. Gillon, J. Org. Chem. 1982, 47, 3297–3306.

    CAS  Google Scholar 

  184. R. D. Clark, C. H. Heathcock, Tetrahedron Lett. 1975, 16, 529–532.

    Google Scholar 

  185. A. Gil de Oliveira Santos, W. Klute, J. Torode, V. P. W. Böhm, E. Cabrita, J. Runsink, R. W. Hoffmann, New. J. Chem. 1998, 993–997.

    Google Scholar 

  186. X. Li, L. B. Schenkel, M. C. Kozlowski, Org. Lett. 2000, 2, 875–878.

    CAS  Google Scholar 

  187. D. P. G. Hannon, R. N. Young, Austr. J. Chem. 1976, 29, 145–161.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to R.W. Hoffmann .

Rights and permissions

Reprints and permissions

Copyright information

© 2009 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Hoffmann, R. (2009). Formation of Cyclic Structures. In: Elements of Synthesis Planning. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-79220-8_6

Download citation

Publish with us

Policies and ethics