The Chemical Synthesis of Discodermolide

  • I. Paterson
  • G. J. Florence
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 286)


The marine sponge-derived polyketide discodermolide is a potent antimitotic agent that represents a promising natural product lead structure in the treatment of cancer. Discodermolide shares the same microtubule-stabilising mechanism of action as Taxol®, inhibits the growth of solid tumours in animal models and shows synergy with Taxol. The pronounced cytotoxicity of discodermolide, which is maintained against cancer cell lines that display resistance to Taxol and other drugs, combined with its scarce availability from its natural source, has fuelled significant academic and industrial interest in devising a practical total synthesis as a means of ensuring a sustainable supply for drug development. This chapter surveys the various total syntheses of discodermolide that have been completed over the period 1993–2007, focusing on the strategies employed for introduction of the multiple stereocentres and achieving control over the alkene geometry, along with the various methods used for realising the pivotal fragment couplings to assemble progressively the full carbon skeleton. This dedicated synthetic effort has triumphed in removing the supply problem for discodermolide, providing sufficient material for extensive biological studies and enabling its early stage clinical development, as well as facilitating SAR studies for lead optimisation.


Anticancer Natural products Polyketides Stereocontrol Tubulin 


  1. 1.
    Blunt JW, Copp BR, Hu WP, Munro MHG, Northcote PT, Prinsep MR (2007) Nat Prod Rep 24:31Google Scholar
  2. 2.
    Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2006) Nat Prod Rep 23:26Google Scholar
  3. 3.
    3 Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2005) Nat Prod Rep 22:15Google Scholar
  4. 4.
    Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2003) Nat Prod Rep 20:1Google Scholar
  5. 5.
    Koehn FE, Carter GT (2005) Nat Rev Drug Discov 4:206Google Scholar
  6. 6.:
    Butler MS (2005) Nat Prod Rep 22:162Google Scholar
  7. 7.
    Newman DJ, Cragg GM (2007) J Nat Prod 70:461Google Scholar
  8. 8.
    Paterson I, Anderson EA (2005) Science 310:451Google Scholar
  9. 9.
    Hamann MT, Hill R, Roggo S (2007) Chimia 61:313Google Scholar
  10. 10.
    Paterson I, Florence GJ (2003) Eur J Org Chem 2193Google Scholar
  11. 11.:
    Mickel SJ (2007) Pure Appl Chem 79:685Google Scholar
  12. 12.:
    Kalesse M (2000) ChemBioChem 1:171Google Scholar
  13. 13.
    Smith AB, Freeze BP (2008) Tetrahedron 64:261Google Scholar
  14. 14.
    Paterson I, Yeung KS (2005) Chem Rev 105:4237Google Scholar
  15. 15.
    Altmann KH, Gertsch J (2007) Nat Prod Rep 24:327Google Scholar
  16. 16.:
    Kuppens IELM (2006) Curr Clin Pharmacol 1:57Google Scholar
  17. 17.
    Gunasekera SP, Gunasekera M, Longley RE, Schulte GK (1990) J Org Chem 55:4912; correction (1991) J Org Chem 56:1346Google Scholar
  18. 18.
    Gunasekera SP, Paul GK, Longley RE, Isbrucker RA, Pomponi SA (2002) J Nat Prod 65:1643Google Scholar
  19. 19.
    Smith AB, LaMarche MJ, Falcone-Hindley M (2001) Org Lett 3:695Google Scholar
  20. 20.
    Longley RE, Caddigan D, Harmody D, Gunasekera M, Gunasekera SP (1991) Transplantation 52:650Google Scholar
  21. 21.
    Longley RE, Caddigan D, Harmody D, Gunasekera M, Gunasekera SP (1991) Transplantation 52:656Google Scholar
  22. 22.
    ter Haar E, Kowalski RJ, Hamel E, Lin CM, Longley RE, Gunasekera SP, Rosenkranz HS, Day BW (1996) Biochemistry 35:243Google Scholar
  23. 23.
    Horwitz SB, Cohen D, Rao S, Shen HJ, Yang CP (1993) J Natl Cancer Inst 15:55Google Scholar
  24. 24.
    Bollag DM, McQueney PA, Zhu J, Hensens O, Koupal L, Liesch J, Goetz M, Lazarides E, Woods CM (1995) Cancer Res 55:2325Google Scholar
  25. 25.
    D'Ambrosio M, Guerriero A, Pietra F (1987) Helv Chim Acta 70:2019Google Scholar
  26. 26.
    Lindel T, Jensen PR, Fencial W, Long BH, Casazza AM, Carboni J, Fairchild CR (1997) J Am Chem Soc 119:8744Google Scholar
  27. 27.
    Mooberry SL, Tien G, Hernez AH, Plubrukarn A, Davidson BS (1999) Cancer Res 59:653Google Scholar
  28. 28.
    Sato B, Nakajima H, Hori Y, Hashimoto S, Terano H (2000) J Antibiot 53:204Google Scholar
  29. 29.
    Hood KA, West LM, Rouwe B, Northcote PT, Berridge MV, Wakefield J, Miller JH (2002) Cancer Res 62:3356Google Scholar
  30. 30.
    Pettit GR, Chicacz ZA, Gao F, Boyd MR, Schmidt JM (1994) J Chem Soc Chem Commun 1111Google Scholar
  31. 31.
    Isbrucker RA, Cummins J, Pomponi SA, Longley RE, Wright AE (2006) Biochem Pharmacol 66:75Google Scholar
  32. 32.
    Paterson I, Britton R, Delgado O, Wright AE (2004) Chem Commun 632Google Scholar
  33. 33.
    Boven E, Venema-Gaberscek E, Erkelens CA, Bissery MC, Pinedo HM (1993) Ann Oncol 4:321Google Scholar
  34. 34.
    Kowalski RJ, Giannakakou P, Gunasekera SP, Longley RE, Day BW, Hamel E (1997) Mol Pharmacol 52:613Google Scholar
  35. 35.
    Schreiber SL, Chen J, Hung DT (1996) Chem Biol 3:287Google Scholar
  36. 36.
    Martello LA, McDaid HM, Regl DL, Yang CH, Meng D, Pettus TRR, Kaufman MD, Arimoto H, Danishefsky SJ, Smith AB, Horowitz SB (2000) Clin Cancer Res 6:1978Google Scholar
  37. 37.
    Huang GS, Lopez-Barcons L, Freeze BS, Smith AB, Goldberg GL, Horwitz SB, McDaid HM (2006) Clin Cancer Res 12:298Google Scholar
  38. 38.
    Sanchez-Pedregal VM, Kubicek K, Meiler J, Lyothier I, Paterson I, Carlomagno T (2006) Angew Chem Intl Ed 45:7388Google Scholar
  39. 39.
    Mita A, Lockhart C, Chen TL, Bocinski K, Curtright J, Cooper W, Hammond L, Rothenberg M, Rowinsky E, Sharma S (2004) ASCO Annual Meeting Proceedings (Post-Meeting Edition) J Clin Oncol 22(14S) (July 15 Suppl) Abstract 2025Google Scholar
  40. 40.
    Altaha R, Fojo T, Reed E, Abraham J (2002) Curr Pharm Design 8:1707Google Scholar
  41. 41. Scholar
  42. 42.:
    Piel J (2004) Nat Prod Rep 21:519Google Scholar
  43. 43.
    Nerenberg JB, Hung DT, Somers PK, Schreiber SL (1993) J Am Chem Soc 115:12621Google Scholar
  44. 44.
    Hung DT, Nerenberg JB, Schreiber SL (1996) J Am Chem Soc 118:11054Google Scholar
  45. 45.
    Smith AB, Qiu YP, Jones DR, Kobayashi K (1995) J Am Chem Soc 117:12011Google Scholar
  46. 46.
    Smith AB, Beauchamp TJ, LaMarche MJ, Kaufman MD, Qiu YP, Arimoto H, Jones DR, Kobayashi K (2000) J Am Chem Soc 122:8654Google Scholar
  47. 47.
    Smith AB, Kaufman MD, Beauchamp TJ, LaMarche MJ, Arimoto H (1999) Org Lett 1:1823Google Scholar
  48. 48.
    Smith AB, Kaufman MD, Beauchamp TJ, LaMarche MJ, Arimoto H (2000) Org Lett 2:1983Google Scholar
  49. 49.
    Smith AB, Freeze BS, Brouard I, Hirose T (2003) Org Lett 5:4405Google Scholar
  50. 50.
    Smith AB, Freeze BS, Xian M, Hirose T (2005) Org Lett 7:1825Google Scholar
  51. 51.
    Harried SS, Yang G, Strawn MA, Myles DC (1997) J Org Chem 62:6098Google Scholar
  52. 52.
    Harried SS, Lee CP, Yang G, Lee TIH, Myles DC (2003) J Org Chem 68:6646Google Scholar
  53. 53.
    Marshall JA, Johns BA (1998) J Org Chem 63:7885Google Scholar
  54. 54.
    Marshall JA, Lu ZH, Johns BA (1998) J Org Chem 63:817Google Scholar
  55. 55.
    Paterson I, Florence GJ, Gerlach K, Scott JP (2000) Angew Chem Intl Ed 39:377Google Scholar
  56. 56.
    Paterson I, Florence GJ (2000) Tetrahedron Lett 41:6935Google Scholar
  57. 57.
    Paterson I, Florence GJ, Gerlach K, Scott JP, Sereinig N (2001) J Am Chem Soc 123:9535Google Scholar
  58. 58.
    Paterson I, Delgado O, Florence GJ, Lyothier I, Scott JP, Sereinig N (2003) Org Lett 5:35Google Scholar
  59. 59.
    Paterson I, Delgado O, Florence GJ, Lyothier I, O'Brien M, Scott JP, Sereinig N (2005) J Org Chem 70:150Google Scholar
  60. 60.
    Paterson I, Lyothier I (2004) Org Lett 6:4933Google Scholar
  61. 61.
    Paterson I, Lyothier I (2005) J Org Chem 70:5494Google Scholar
  62. 62.
    Arefolov A, Panek JS (2005) J Am Chem Soc 127:5596Google Scholar
  63. 63.
    Arefolov A, Panek JS (2002) Org Lett 4:2397Google Scholar
  64. 64.
    de Lemos E, Por Ée FH, Commerçon A, Betzer JF, Pancrazi A, Ardisson J (2007) Angew Chem Intl Ed 46:1917Google Scholar
  65. 65.
    Mickel SJ, Sedelmeier GH, Niederer D, Daeffler R, Osmani A, Schreiner K, Seeger-Weibel M, B Érod B, Schaer K, Gamboni R, Chen S, Chen W, Jagoe CT, Kinder FR, Loo M, Prasad K, Repic O, Shieh W-C, Wang R-M, Waykole L, Xu DD, Xue S (2004) Org Process Res Dev 8:92Google Scholar
  66. 66.
    Mickel SJ, Sedelmeier GH, Niederer D, Schuerch F, Grimler D, Koch G, Daeffler R, Osmani A, Hirni A, Schaer K, Gamboni R, Bach A, Chaudhary A, Chen S, Chen W, Hu B, Jagoe CT, Kim H-Y, Kinder FR, Liu Y, Lu Y, McKenna J, Prashad M, Ramsey T M, Repic O, Rogers L, Shieh W-C, Wang R-M, Waykole L (2004) Org Process Res Dev 8:101Google Scholar
  67. 67.
    Mickel SJ, Sedelmeier GH, Niederer D, Schuerch F, Koch G, Kuesters E, Daeffler R, Osmani A, Seeger-Weibel M, Schmid E, Hirni A, Schaer K, Gamboni R, Bach A, Chen S, Chen W, Geng P, Jagoe CT, Kinder FR, Lee GT, McKenna J, Ramsey TM, Repic O, Rogers L, Shieh W-C, Wang R-M, Waykole L (2004) Org Process Res Dev 8:107Google Scholar
  68. 68.
    Mickel SJ, Sedelmeier GH, Niederer D, Schuerch F, Seger M, Schreiner K, Daeffler R, Osmani A, Bixel D, Loiseleur O, Cercus J, Stettler H, Schaer K, Gamboni R, Bach A, Chen G-P, Chen W, Geng P, Lee GT, Loeser E, McKenna J, Kinder FR, Konigsberger K, Prasad K, Ramsey TM, Reel N, Repic O, Rogers L, Shieh W-C, Wang R-M, Waykole L, Xue S, Florence G, Paterson I (2004) Org Process Res Dev 8:113Google Scholar
  69. 69.
    Mickel SJ, Niederer D, Daeffler R, Osmani A, Kuesters E, Schmid E, Schaer K, Gamboni R, Chen W, Loeser E, Kinder FR, Konigsberger K, Prasad K, Ramsey TM, Repic O, Wang R-M, Florence G, Lyothier I, Paterson I (2004) Org Process Res Dev 8:122Google Scholar
  70. 70.
    Paterson I, Wren SP (1993) J Chem Soc Chem Commun 1790Google Scholar
  71. 71.
    Clark DL, Heathcock CH (1993) J Org Chem 58:5878Google Scholar
  72. 72.
    Golec JMC, Jones SD (1993) Tetrahedron Lett 34:8159Google Scholar
  73. 73.
    Evans PL, Golec JMC, Gillespie RJ (1993) Tetrahedron Lett 34:8163Google Scholar
  74. 74.
    Golec JMC, Gillespie RJ (1993) Tetrahedron Lett 34:8167Google Scholar
  75. 75.
    Paterson I, Schlapbach A (1995) Synlett 498Google Scholar
  76. 76.
    Miyazawa M, Oonuma S, Maruyama K, Miyashita M (1997) Chem Lett 1191Google Scholar
  77. 77.
    Miyazawa M, Oonuma S, Maruyama K, Miyashita M (1997) Chem Lett 1193Google Scholar
  78. 78.
    Misske AM, Hoffmann HMR (1999) Tetrahedron 55:4315Google Scholar
  79. 79.
    Evans DA, Halstead DP, Allison BD (1999) Tetrahedron Lett 40:4461Google Scholar
  80. 80.
    Filla SA, Song JJ, Chen LR, Masamune S (1999) Tetrahedron Lett 40:5449Google Scholar
  81. 81.
    Yadav JS, Abraham S, Reddy MM, Sabitha G, Sankar AR, Kunwar AC (2001) Tetrahedron Lett 42:4713. Correction (2002) Tetrahedron Lett 43:3453Google Scholar
  82. 82.
    Arjona O, Menchaca R, Plumet J (2001) Tetrahedron 57:6751Google Scholar
  83. 83.
    BouzBouz S, Cossy J (2001) Org Lett 3:3995Google Scholar
  84. 84.
    Chakraborty TK, Laxman P (2001) J Indian Chem Soc 78:543Google Scholar
  85. 85.
    Shahid KA, Li YN, Okazaki M, Shuto Y, Goto F, Kiyooka S (2002) Tetrahedron Lett 43:6373Google Scholar
  86. 86.
    Shahid KA, Mursheda J, Okazaki M, Shuto Y, Goto F, Kiyooka S (2002) Tetrahedron Lett 43:6377. Correction (2003) Tetrahedron Lett 44:1519Google Scholar
  87. 87.
    Day BW, Kangani CO, Avor KS (2002) Tetrahedron-Asymmetry 13:1161Google Scholar
  88. 88.
    Yakura T, Kitano T, Ikeda M, Uenishi J (2003) Heterocycles 59:347Google Scholar
  89. 89.
    Kiyooka S-I, Shahid KA, Goto F, Okazaki M, Shuto Y (2003) J Org Chem 68:7967Google Scholar
  90. 90.
    Francavilla C, Chen W, Kinder FR (2003) Org Lett 5:1233Google Scholar
  91. 91.
    Baz Àn-Tejeda B, Georgy M, Campagne J-M (2004) Synlett 720Google Scholar
  92. 92.
    Loiseleur O, Koch G, Wagner T (2004) Org Process Res Dev 8:597Google Scholar
  93. 93.
    BouzBouz S, Cossy J (2004) Synlett 2034Google Scholar
  94. 94.
    Ramachandran PV, Prabhudas B, Chandra JS, Reddy MVR (2004) J Org Chem 69:6294Google Scholar
  95. 95.
    Loiseleur O, Koch G, Cercus J, Sch örch F (2005) Org Process Res Dev 9:259Google Scholar
  96. 96.
    Parker KA, Cao H (2006) Org Lett 8:3541Google Scholar
  97. 97.
    Burlingame MA, Mendoza E, Ashley GW, Myles DC (2006) Tetrahedron Lett 47:1209Google Scholar
  98. 98.
    Aicher TD, Kishi Y (1987) Tetrahedron Lett 28:3463Google Scholar
  99. 99.
    Takai K, Kuroda T, Nakatsukasa S, Oshima K, Nozaki H (1985) Tetrahderon Lett 26:5585Google Scholar
  100. 100.
    Takai K, Tagashira M, Kuroda T, Oshima K, Utimoto K, Nozaki H (1986) J Am Chem Soc 108:6048Google Scholar
  101. 101.
    Jin H, Uenishi J, Christ WJ, Kishi Y (1986) J Am Chem Soc 108:5644Google Scholar
  102. 102.
    Roush WR, Palkowitz AD, Ando K (1990) J Am Chem Soc 112:6348Google Scholar
  103. 103.
    Evans DA, Gauchet-Prunet JA (1993) J Org Chem 58:2446Google Scholar
  104. 104.
    Stork G, Zhao K (1989) Tetrahedron Lett 30:2173Google Scholar
  105. 105.
    Negishi E, Valente LF, Kobayashi M (1980) J Am Chem Soc 102:3298Google Scholar
  106. 106.
    Still WC, Gennari C (1983) Tetrahedron Lett 24:4405Google Scholar
  107. 107.
    Hung DT, Nerenberg JB, Schreiber SL (1994) Chem Biol 1:67Google Scholar
  108. 108.
    Evans DA, Bartoli JA, Shih TL (1981) J Am Chem Soc 103:2127Google Scholar
  109. 109.
    Evans DA, Takacs JM, McGee LR, Ennis MD, Mathre DJ, Bartoli JA (1981) Pure Appl Chem 53:1109Google Scholar
  110. 110.
    Gage JR, Evans DA (1990) Org Syn 68:77Google Scholar
  111. 111.
    Gage JR, Evans DA (1990) Org Syn 68:83Google Scholar
  112. 112.
    Chen J, Wang T, Zhao K (1994) Tetrahedron Lett 35:2827Google Scholar
  113. 113.
    Arimoto H, Kaufman MD, Kobayashi K, Qiu YP, Smith AB (1998) Synlett 765Google Scholar
  114. 114.
    Evans DA, Chapman KT, Carreira EM (1998) J Am Chem Soc 110:3560Google Scholar
  115. 115.
    Ikeda Y, Ukai J, Ikeda N, Yamamoto H (1987) Tetrahedron 43:723Google Scholar
  116. 116.
    Miyaura N, Suzuki A (1995) Chem Rev 95:2457Google Scholar
  117. 117.
    Brown HC, Bhat KS (1986) J Am Chem Soc 108:293Google Scholar
  118. 118.
    Danishefsky SJ, Larson E, Askin D, Kato N (1985) J Am Chem Soc 107:1246Google Scholar
  119. 119.
    Luche JL, Gemal AL (1979) J Am Chem Soc 101:5848Google Scholar
  120. 120.
    Gemal AL, Luche JL (1981) J Am Chem Soc 103:5454Google Scholar
  121. 121.
    Ferrier RJ (1964) J Chem Soc 5443Google Scholar
  122. 122.
    Keck GE, Abbott DE (1984) Tetrahedron Lett 25:1883Google Scholar
  123. 123.
    Linderman RJ, Cusack KP, Jaber MR (1996) Tetrahedron Lett 37:6649Google Scholar
  124. 124.
    White JD, Nylund CS, Green NJ (1997) Tetrahedron Lett 38:7329Google Scholar
  125. 125.
    Roush WR, Grover PT (1992) Tetrahedron 48:1981Google Scholar
  126. 126.
    Tsai DJ-S, Matteson DS (1981) Tetrahedron Lett 22:2751Google Scholar
  127. 127.
    Chen CP, Tagami K, Kishi Y (1995) J Org Chem 60:5386Google Scholar
  128. 128.
    Marshall JA, Perkins JF, Wolf MA (1995) J Org Chem 60:5556Google Scholar
  129. 129.
    Marshall JA, Palovich MR (1997) J Org Chem 62:6001Google Scholar
  130. 130.
    Paterson I, Norcross RD, Ward RA, Romea P, Lister MA (1994) J Am Chem Soc 116:11287Google Scholar
  131. 131.
    Paterson I, Wallace DJ, Cowden CJ (1998) Synthesis 639Google Scholar
  132. 132.
    Paterson I, Lister MA (1988) Tetrahedron Lett 29:585Google Scholar
  133. 133.
    Paterson I, Channon J (1992) Tetrahedron Lett 33:797Google Scholar
  134. 134.
    Paterson I, Tillyer RD (1992) Tetrahedron Lett 33:4233Google Scholar
  135. 135.
    Paterson I, Goodman JM, Isaka M (1989) Tetrahedron Lett 30:7121Google Scholar
  136. 136.
    Paterson I, Arnott EA (1998) Tetrahedron Lett 39:7185Google Scholar
  137. 137.
    Paterson I, Wallace DJ, Vel Àzquez SM (1994) Tetrahedron Lett 35:9083Google Scholar
  138. 138.
    Paterson I, Wallace DJ (1994) Tetrahedron Lett 35:9087Google Scholar
  139. 139.
    Cowden CJ, Paterson I (1997) Org React 51:1Google Scholar
  140. 140.
    Carling RW, Holmes AB (1986) J Chem Soc Chem Commun 325Google Scholar
  141. 141.
    Curtis NR, Holmes AB, Looney MG (1991) Tetrahedron 47:7171Google Scholar
  142. 142.
    Holmes AB, Looney MG (1993) J Am Chem Soc 115:5815Google Scholar
  143. 143.
    Fuhry MAM, Holmes AB, Marshall DR (1993) J Chem Soc Perkin Trans 1:2743Google Scholar
  144. 144.
    Burton JW, Clark JS, Derrer S, Stork TC, Bendall JG, Holmes AB (1999) Synlett 972Google Scholar
  145. 145.
    Paterson I, Perkins MV (1996) Tetrahedron 52:1811Google Scholar
  146. 146.
    Paterson I, Perkins MV (1992) Tetrahedron Lett 33:801Google Scholar
  147. 147.
    Pirrung MC, Heathcock CH (1980) J Org Chem 45:1727Google Scholar
  148. 148.:
    Paterson I (1983) Tetrahedron Lett 24:1311Google Scholar
  149. 149.
    De Mico A, Margarita R, Parlanti L, Vescovi A, Piancatelli G (1997) J Org Chem 62:6974Google Scholar
  150. 150.
    Paterson I, Goodman JM, Lister MA, Schumann RC, McClure CK, Norcross RD (1990) Tetrahedron 46:4663Google Scholar
  151. 151.
    Paterson I, Cumming JG, Smith JD, Ward RA (1994) Tetrahedron Lett 35:441Google Scholar
  152. 152.
    Paterson I, Oballa RM, Norcross RD (1996) Tetrahedron Lett 37:8581Google Scholar
  153. 153.
    Paton, RS, Goodman JM (2006) Org Lett 8:4299Google Scholar
  154. 154.
    Wensheng Y, Su M, Jin Z (1999) Tetrahedron Lett 40:6725Google Scholar
  155. 155.
    Jain NF, Takenaka N, Panek JS (1996) J Am Chem Soc 118:12475Google Scholar
  156. 156.
    Jain NF, Crillo PF, Pelletier R, Panek JS (1995) Tetrahedron Lett 36:8727Google Scholar
  157. 157.
    Masse CE, Panek JS (1995) Chem Rev 95:1293Google Scholar
  158. 158.
    Panek JS, Beresis RT (1993) J Org Chem 58:809Google Scholar
  159. 159.
    Panek JS, Crillo PF (1993) J Org Chem 58:294Google Scholar
  160. 160.
    Hart DW, Schwartz J (1974) J Am Chem Soc 96:8115Google Scholar
  161. 161.
    Buchwald SL, LaMaire SJ, Nielsen RB, Watson BT, King SM (1987) Tetrahedron Lett 28:3895Google Scholar
  162. 162.
    Paterson I, Gibson KR, Oballa, RM (1996) Tetrahedron Lett 47:8585Google Scholar
  163. 163.
    Evans DA, Coleman PJ, C Ôt É B (1997) J Org Chem 62:788Google Scholar
  164. 164.
    Evans DA, Hoveyda AH (1990) J Am Chem Soc 112:6447Google Scholar
  165. 165.
    Tomioka H, Takai K, Oshima K, Nozaki H (1981) Tetrahedron Lett 22:1605Google Scholar
  166. 166.:
    Hoppe D (1984) Angew Chem 96:930Google Scholar
  167. 167.
    Hoppe D, Hense T (1997) Angew Chem 109:2376Google Scholar
  168. 168.
    Hoppe D, Zchage O (1989) Angew Chem 101:67Google Scholar
  169. 169.
    Hoppe D, Zchage O (1992) Tetrahedron 48:8389Google Scholar
  170. 170.
    Fargeas V, Le M Énez P, Berque I, Ardisson J, Pancrazi A (1996) Tetrahedron 52:6613Google Scholar
  171. 171.
    Berque I, Le MÉnez P, Razon P, Mahuteau J. Férézou J-P, J-P, Pancrazi A, Ardisson J, Brion J-D (1999) J Org Chem 64:373Google Scholar
  172. 172.
    Kocienski P, Wadman S, Cooper K (1989) J Am Chem Soc 111:2363Google Scholar
  173. 173.
    Kocienski P, Barber C (1990) Pure Appl Chem 62:1933Google Scholar
  174. 174.
    Le MÉnez P, Fargeas V, Berque I, Poisson J, Ardisson J, Lallem JY, Pancrazi A (1995) J Org Chem 60:3592Google Scholar
  175. 175.
    Fargeas V, Le M Énez P, Berque I, Ardisson J, Pancrazi A (1996) Tetrahedron 52:6613Google Scholar
  176. 176.:
    Braun M (1998) Angew Chem Int Ed 37:430Google Scholar
  177. 177.:
    Knorr R (2004) Chem Rev 104:3795Google Scholar
  178. 178.
    Corey EJ, Bakshi RK, Shibata S (1987) J Am Chem Soc 109:5551Google Scholar
  179. 179.:
    Kaminski ZJ (1987) Synthesis 10:917Google Scholar
  180. 180.
    Kaminski ZJ, Paneth P, Rudzinski J (1998) J Org Chem 63:424Google Scholar
  181. 181.
    Mickel SJ, Daeffler R, Prikoszovich W (2005) Org Process Res Dev 9:113Google Scholar
  182. 182.
    Panek JS, Beresis RT, Xu F, Yang M (1991) J Org Chem 56:7391Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2008

Authors and Affiliations

  1. 1.University Chemical LaboratoryCambridge CB2 1EWUK
  2. 2.School of Chemistry and Centre for Biomolecular Sciences University of St AndrewsNorth HaughUK

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