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Electrophilic Substitution Reactions of Indoles

  • Richard J. SundbergEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 26)

Abstract

The topic of this chapter is electrophilic substitution of indole and its derivatives. The indole ring is highly reactive at its 3-position toward protonation, halogenation, alkylation and acylation. Electrophilic substitution can be combined with inter- or intramolecular addition at C-2. Intramolecular alkylation by iminium ions (Pictet-Spengler reaction) is particularly useful. Enantioselectivity can be achieved in many conjugate addition reactions. These reactions have been applied to synthesis of both natural products and drugs.

Keywords

Acylation Alkylation Aminoalkylation Conjugate addition Electrophilic substitution Halogenations Indole 

References

  1. 1.
    Mayr H, Kempf B, Ofial AR (2003) Acc Chem Res 36:66–77Google Scholar
  2. 2.
    Lakhdar S, Westermaier M, Terrier F, Goumont R, Boubaker T, Ofial AR, Mayr H (2006) J Org Chem 71:9088–9095Google Scholar
  3. 3.
    Kempf B, Hampel N, Ofial AR, Mayr H (2003) Chem Eur J 9:2209–2218Google Scholar
  4. 4.
    Terrier F, Kizilian E, Halle J-C, Buncel E (1992) J Am Chem Soc 114:1740–1742Google Scholar
  5. 5.
    Terrier F, Pouet M-J, Halle J-C, Hunt S, Jones JR, Buncel E (1993) J Chem Soc Perkin Trans 2:1665–1672Google Scholar
  6. 6.
    Rodrigues-Dafonte P, Terrier F, Lakhdar S, Kurbatov S, Goumont R (2009) J Org Chem 74:3305–3315Google Scholar
  7. 7.
    Abdullah MI, Jackson AH, Lynch PP, Record KAF (1990) Heterocycles 30:317–320Google Scholar
  8. 8.
    Gazquez JL, Mendez F, (1994) J Phys Chem 98:4591–4593Google Scholar
  9. 9.
    Martinez A, Vazquez M-V, Carreon-Macedo JL, Sansores LE, Salcedo R (2003) Tetrahedron 59:6415–6422Google Scholar
  10. 10.
    Hinman RL, Lang J (1964) J Am Chem Soc 86:3796–3806Google Scholar
  11. 11.
    Andonovski BS, Stajkovic GM (1999) J Serbian Chem Soc 64:775–787Google Scholar
  12. 12.
    Hoyuelos FJ, Garcia B, Ibeas S, Munoz MS, Navaro AM, Penacoba I, Leal JM (2005) Eur J Org Chem:1161–1171Google Scholar
  13. 13.
    Cohen PA, Cohen LA (1992) Can J Chem 70:282–284Google Scholar
  14. 14.
    Guidotti S, Camurati I, Focante F, Angellini L, Moscardi G, Resconi L, Leardini R, Nanni D, Mercandelli P, Sironi A, Beringhelli T, Maggioni D (2003) J Org Chem 68:5445–5465Google Scholar
  15. 15.
    Hodson HF, Smith GF (1957) J Chem Soc:3544–3545Google Scholar
  16. 16.
    Noland WE, Kuryla WC (1960) J Org Chem 25:486–487Google Scholar
  17. 17.
    Quartarone G, Ronchin L, Tortato C, Vavasori A (2009) Int J Chem Kinet 41:107–112Google Scholar
  18. 18.
    Ishii H, Murakami K, Sakurada E, Hosoya K, Murakami Y (1988) J Chem Soc Perkin Trans 1:2377–2385Google Scholar
  19. 19.
    Banerji J, Saha M, Kanrar S, Mukherjee P (1995) Indian J Chem 34B:1095–1097Google Scholar
  20. 20.
    Pal B, Giri VS, Jaisankar P (2005) Catal Commun 6:711–715Google Scholar
  21. 21.
    Bergman J, Koch E, Pelcman B (1995) Tetrahedron Lett 36:3945–3948Google Scholar
  22. 22.
    Fatum TM, Anthoni U, Christophersen C, Nielsen PH (1998) Acta Chem Scand 52:784–789Google Scholar
  23. 23.
    Gilbert EJ, Ziller JW, Van Vranken DL (1997) Tetrahedron 53:16553–16561Google Scholar
  24. 24.
    McComas CC, Gilbert EJ, Van Vranken DL (1997) J Org Chem 62:8600–8603Google Scholar
  25. 25.
    Tajima N, Hayashi T, Nakatsuka S (2000) Tetrahedron Lett 41:1059–1062Google Scholar
  26. 26.
    Phillips RS, Sundararaju B, Faleev NG (2000) J Am Chem Soc 122:1008–1014Google Scholar
  27. 27.
    Gribble GW (2006) In: Li JJ, Gribble GW (eds) Palladium in heterocyclic chemistry, 2nd edn. Elsevier, Oxford, pp 81–188Google Scholar
  28. 28.
    Kirk KL (2005) Am Chem Soc Symp Ser 911:303–316Google Scholar
  29. 29.
    Tsotinis A, Eleutheriades A, Davidson K, Sugden D (2007) Curr Drug Discov Technol 4:198–207Google Scholar
  30. 30.
    Gribble GW (2003) Prog Heterocycl Chem 15:58–79Google Scholar
  31. 31.
    Gribble GW (2008) In: Fattorusso E, Taglialatel-Scafati O (eds) Modern alkaloids, structure, isolation synthesis and biology. Wiley-VCH, Weinheim, pp 591–618Google Scholar
  32. 32.
    Humphrey GR, Kuethe JT (2006) Chem Rev 106:2875–2911Google Scholar
  33. 33.
    DeRosa M, Triana Alonso JL (1978) J Org Chem 43:2639–2643Google Scholar
  34. 34.
    Brennan MR, Erickson KL, Szmalc FS, Tanse MJ, Thornton JM (1986) Heterocycles 24:2879–2885Google Scholar
  35. 35.
    Ohta T, Somei M (1989) Heterocycles 29:1163–1667Google Scholar
  36. 36.
    Mistry AG, Smith K, Bye MR (1986) Tetrahedron Lett 27:1051–1054Google Scholar
  37. 37.
    Piers K, Meimaroglou C, Jardine RV, Brown RK (1963) Can J Chem 41:2399–2401Google Scholar
  38. 38.
    Bocchi V, Palla G (1982) Synthesis:1096–1097Google Scholar
  39. 39.
    Arnold RD, Nutter WM, Stepp WL (1959) J Org Chem 24:117–118Google Scholar
  40. 40.
    Takeuchi Y, Tauri T, Shibata N (2000) Org Lett 2:639–642Google Scholar
  41. 41.
    Baudoux J, Salit A-F, Cahard D, Plaquevent J-C (2002) Tetrahedron Lett 43:6573–6574Google Scholar
  42. 42.
    Shibata N, Suzuki E, Asahi T, Shiro M (2001) J Am Chem Soc 123:7001–7009Google Scholar
  43. 43.
    Hodgson HF, Madge DJ, Slawin ANZ, Widdowson DA, Williams DJ (1994) Tetrahedron 50:1899–1906Google Scholar
  44. 44.
    Hayakawa Y, Singh M, Shibata N, Takeuchi Y, Kirk KL (1997) J Fluor Chem 97:161–164Google Scholar
  45. 45.
    Williams JD, Chen JJ, Drach JC, Townsend LB (2004) J Med Chem 47:5733–5765Google Scholar
  46. 46.
    Hinman RL, Bauman CP (1964) J Org Chem 29:1206–1215Google Scholar
  47. 47.
    Chattise PK, Ramaswamy AV, Waghmode SB (2008) Tetrahedron Lett 49:189–194Google Scholar
  48. 48.
    Amat M, Hadida S, Sathyananrayana S, Bosch J (1994) J Org Chem 59:10–11Google Scholar
  49. 49.
    Amat M, Sathyanarayana S, Hadida S, Bosch J (1996) Heterocycles 43:1713–1718Google Scholar
  50. 50.
    Tang S, Li J-H, Xie Y-X, Wang N-X (2007) Synthesis:1535–1541Google Scholar
  51. 51.
    Bergman J, Venemalm L (1992) J Org Chem 57:2495–2497Google Scholar
  52. 52.
    Lu Y, Gribble GW (2002) J Nat Prod 65:748–749Google Scholar
  53. 53.
    Gribble GW, Allison BD, Conway SC, Saulnier MG (1992) Org Prep Proced Int 24:649–654Google Scholar
  54. 54.
    Saulnier MG, Gribble GW (1982) J Org Chem 47:757–761Google Scholar
  55. 55.
    Lachance N, Chan WY (2003) J Heterocycl Chem 40:289–295Google Scholar
  56. 56.
    Tani M, Ikegami H, Tashiro M, Hiura T, Tsukioka H, Kaneko C, Notoya T, Shimizu M, Uchida M, Aida Y, Yokoyama Y, Murakami Y (1992) Heterocycles 34:2349–2362Google Scholar
  57. 57.
    Kruse LI, Meyer MD (1984) J Org Chem 49:4761–4768Google Scholar
  58. 58.
    Tois J, Franzen R, Aitio O, Laakso I, Huuskonen J, Taskinen J (2001) Comb Chem High Throughput Screen 4:521–524Google Scholar
  59. 59.
    Ezquerra J, Pedregal C, Lamas C, Barluenga J, Perez M, Garcia-Martin MA, Gonzalez J (1996) J Org Chem 61:5804–5812Google Scholar
  60. 60.
    Benhida R, Blanchard P, Fourrey J-L (1998) Tetrahedron Lett 39:6849–6852Google Scholar
  61. 61.
    Harrington PJ, Hegedus LS (1984) J Org Chem 49:2657–2662Google Scholar
  62. 62.
    Putey A, Popowycz F, Joseph B (2007) Synlett:419–422Google Scholar
  63. 63.
    Lista L, Pezzella A, Napolitano A, d’Ischia M (2008) Tetrahedron 64:234–239Google Scholar
  64. 64.
    Mohanakrishnan AK, Prakash C, Ramesh N (2006) Tetrahedron 62:3242–3247Google Scholar
  65. 65.
    Snider BB, Zang H (2003) J Org Chem 68:545–563Google Scholar
  66. 66.
    Coste A, Toumi M, Wright K, Razafimahaleo V, Couty F, Marrot J, Evano G (2008) Org Lett 10:3841–3844Google Scholar
  67. 67.
    Brown MA, Kerr MA (2001) Tetrahedron Lett 42:983–985Google Scholar
  68. 68.
    Scheryantz JM, Woo JCG, Silphaivanh P, Depew KM, Danishefsky SJ (1999) J Am Chem Soc 121:11964–11975Google Scholar
  69. 69.
    Martinez JS, Carroll GL, Tschirret-Guth RA, Altenhoff G, Little RD, Butler A (2001) J Am Chem Soc 123:3289–3294Google Scholar
  70. 70.
    Butler A, Carter-Franklin JN (2004) Nat Prod Res 21:180–188Google Scholar
  71. 71.
    Butler A (1998) Curr Opin Chem Biol 2:279–285Google Scholar
  72. 72.
    Dong C, Flecks S, Unversucht S, Haupt C, Pee K-H, Naismith JH (2005) Science 309:2216–2219Google Scholar
  73. 73.
    Yeh E, Garneau S, Walsh CT (2005) Proc Natl Acad Sci USA 102:3960–3965Google Scholar
  74. 74.
    Gilow HM, Brown CS, Copeland JN, Kelly KE (1991) J Heterocycl Chem 28:1025–1034Google Scholar
  75. 75.
    Yadav JS, Reddy BVS, Shubashree S, Sadashiv K (2004) Tetrahedron Lett 45:2951–2954Google Scholar
  76. 76.
    Wu J, Wu G, Wu L (2008) Synth Commun 38:2367–2373Google Scholar
  77. 77.
    Yadav JS, Subba Reddy BV, Murali Krishna BB (2008) Synthesis:3779–3782Google Scholar
  78. 78.
    Dohi T, Morimoto K, Takenaga N, Goto A, Maruyama A, Kiyono Y, Tohma H, Kita Y (2007) J Org Chem 72:109–116Google Scholar
  79. 79.
    Hofmann M, Hampel N, Kanzian T, Mayr H (2004) Angew Chem Int Ed 43:5402–5405Google Scholar
  80. 80.
    Chung JYL, Mancheno D, Dorman PG, Variankaval N, Ball RG, Tsou NN (2008) Org Lett 10:3037–3040Google Scholar
  81. 81.
    Goverdhan G, Raghupati A, Sampath A, Srinivas K, Himabindu V, Reddy GM (2009) Org Process Res Dev 13:67–72Google Scholar
  82. 82.
    Wenkert E, Angell EC, Ferreira VF, Michelotti EL, Piettre SR, Sheu J-H, Swindell CS (1986) J Org Chem 51:2343–2351Google Scholar
  83. 83.
    Bodwell GJ, Li J (2002) Org Lett 4:127–130Google Scholar
  84. 84.
    Mirand C, de Maindreville MD, Levy J (1985) Tetrahedron Lett 26:3985–3988Google Scholar
  85. 85.
    Mitchell MO, Dorroh P (1991) Tetrahedron Lett 32:7641–7642Google Scholar
  86. 86.
    Dix AV, Meseck CM, Lowe AJ, Mitchell MO (2006) Bioorg Med Chem Lett 16:2522–2524Google Scholar
  87. 87.
    Westermaier M, Mayr H (2006) Org Lett 8:4791–4794Google Scholar
  88. 88.
    Zhu X, Ganesan A (2002) J Org Chem 67:2705–2708Google Scholar
  89. 89.
    Tan GH, Zhu X, Ganesan A (2003) Org Lett 5:1801–1803Google Scholar
  90. 90.
    Lopez-Alvarado P, Caballero E, Avendano C, Carlos-Menendez J (2006) Org Lett 8:4303–4306Google Scholar
  91. 91.
    Yadav JS, Reddy BVS, Reddy PM, Srinivas C (2002) Tetrahedron Lettt 43:5185–5187Google Scholar
  92. 92.
    Prajapati D, Gohain M, Gogoi BJ (2006) Tetrahedron Lett 47:3535–3539Google Scholar
  93. 93.
    Henry KJ Jr, Grieco PA (1993) J Chem Soc Chem Commun:510–512Google Scholar
  94. 94.
    Kimura M, Futamata M, Mukai R, Tamaru Y (2005) J Am Chem Soc 127:4592–4593Google Scholar
  95. 95.
    Kimura M, Mukai R, Tanigawa N, Tanaka S, Tamaru Y (2003) Tetrahedron 59:7767–7777Google Scholar
  96. 96.
    Trost BM, Quancard J (2006) J Am Chem Soc 128:6314–6315Google Scholar
  97. 97.
    Bandini M, Melloni A, Umani-Ronchi A (2004) Org Lett 6:3199–3202Google Scholar
  98. 98.
    Luzung MR, Lewis CA, Baran PS (2009) Angew Chem Int Ed 48:7025–7029Google Scholar
  99. 99.
    Schkeryantz JM, Woo JCG, Danishefsky SJ (1999) J Am Chem Soc 121:11964–11975Google Scholar
  100. 100.
    Schkeryantz JM, Woo JCG, Siliphaivanh P, Depew KM, Danishefsky SJ (1995) J Am Chem Soc 117:7025–7026Google Scholar
  101. 101.
    Hewitt RR, Cleator E, Ley SV (2001) Org Biomol Chem 2:2415–2417Google Scholar
  102. 102.
    Liu K, Wood HB, Jones AB (1999) Tetrahedron Lett 40:5119–5122Google Scholar
  103. 103.
    Grubbs AW, Artman GD III, Williams RM (2005) Tetrahedron Lett 46:9013–9016Google Scholar
  104. 104.
    Li SM (2009) Phytochemistry 70:1746–1757Google Scholar
  105. 105.
    Luk LYP, Tanner ME (2009) J Am Chem Soc 131:13932–13933Google Scholar
  106. 106.
    Ruan H-L, Stec E, Li S-M (2009) Arch Microbiol 191:791–795Google Scholar
  107. 107.
    Li SM (2009) Appl Microbiol Biotech 84:631–639Google Scholar
  108. 108.
    Steffan N, Grundman A, Yin W-B, Kremer A, Li SM (2009) Curr Med Chem 16:218–231Google Scholar
  109. 109.
    Zhao X, Yu Z, Xu T, Wu P, Yu H (2007) Org Lett 9:5263–5266Google Scholar
  110. 110.
    Jackson AH, Naidoo B, Smith P (1968) Tetrahedron 24:6119–6129Google Scholar
  111. 111.
    Ganesan A, Heathcock CH (1993) Tetrahedron Lett 34:439–440Google Scholar
  112. 112.
    Baran PS, Richter JM (2004) J Am Chem Soc 126:7450–7451Google Scholar
  113. 113.
    Ferreira EM, Stoltz BM (2003) J Am Chem Soc 125:9578–9579Google Scholar
  114. 114.
    Liu C, Han X, Wang X, Widenhoefer RA (2004) J Am Chem Soc 126:3700–3701Google Scholar
  115. 115.
    Albbiati G, Beccalli EM, Broggini G, Zoni C (2003) J Org Chem 68:7625–7628Google Scholar
  116. 116.
    Bandini M, Melloni A, Piccinelli F, Sinisi R, Tommasi S, Umani-Ronchi A (2006) J Am Chem Soc 128:1424–1425Google Scholar
  117. 117.
    Williams RM, Cao J, Tsujishima H (2000) Angew Chem Int Ed 39:2540–2544Google Scholar
  118. 118.
    Huang H, Peters R (2009) Angew Chem Int Ed 48:604–606Google Scholar
  119. 119.
    Frebault F, Simpkins NS, Fenwick A (2009) J Am Chem Soc 131:4214–4215Google Scholar
  120. 120.
    Mahadevan A, Sard H, Gonzalez M, McKew J (2003) Tetrahedron Lett 44:4589–4591Google Scholar
  121. 121.
    Campbell JA, Bordunov V, Broka CA, Dankwardt J, Hendricks RT, Kress JM, Walker KAM, Wang J-H (2004) Tetrahedron Lett 45:3793–3796Google Scholar
  122. 122.
    Zhuang W, Gathergood N, Hazell RG, Jorgenson KA (2001) J Org Chem 66:1009–1013Google Scholar
  123. 123.
    Bandini M, Sinisi R (2009) Org Lett 11:2093–2096Google Scholar
  124. 124.
    Nie J, Zhang G-W, Wang L, Fu A, Zheng Y, Ma J-A (2009) Chem Commun:2356–2358Google Scholar
  125. 125.
    Chakrabarty M, Karmakar S, Harigaya Y (2005) Heterocycles 65:37–48Google Scholar
  126. 126.
    Jaisankar P, Srinivasan PC (2005) Synth Commun 35:923–927Google Scholar
  127. 127.
    Sheng S-R, Wang Q-Y, Ding Y, Liu X-L, Cai M-Z (2009) Catalysis Lett 128:418–422Google Scholar
  128. 128.
    Peng Y-Y, Zhang Q-L, Yuan J-J, Cheng J-P (2008) Chinese J Chem 26:2228–2232Google Scholar
  129. 129.
    Hazarika P, Das Sharma S, Donwar D (2008) Synth Commun 38:2870–2880Google Scholar
  130. 130.
    Raju BC, Rao JM (2008) Indian J Chem 47B:623–625Google Scholar
  131. 131.
    Magesh CJ, Nagarajan R, Karthik M, Perumal PT (2004) Appl Catal A 266:1–10Google Scholar
  132. 132.
    Feng X-L, Guan C-J, Zhao C-X (2004) Synth Commun 34:487–492Google Scholar
  133. 133.
    Nagarajan R, Perumal PT (2004) Chem Lett 33:288–289Google Scholar
  134. 134.
    Reddy BM, Sreekanth PM, Lakshmanan P (2005) J Mol Catal A 237:93–100Google Scholar
  135. 135.
    Zeng X-F, Ji S-J (2006) Lett Org Chem 3:374–378Google Scholar
  136. 136.
    Li W-J, Lin X-F, Wang J, Li G-L, Wang Y-G (2005) Synth Commun 35:2765–2769Google Scholar
  137. 137.
    Singh P, Singh D, Samant S (2005) Synth Commun 35:2133–2138Google Scholar
  138. 138.
    Azizian J, Teimouri F, Mohamadizadeh MR (2007) Catal Commun 8:1117–1121Google Scholar
  139. 139.
    Nagarajan R, Perumal PT (2002) Synth Commun 32:105–109Google Scholar
  140. 140.
    Yadav JS, Reddy BVS, Murthy CVSR, Kumar GM, Madan C (2001) Synthesis:783–787Google Scholar
  141. 141.
    More UB, Sonawane BS, Mahulikar PP (2008) Org Chem 4:483–485Google Scholar
  142. 142.
    Nasreen A, Varala R, Adap SR (2007) J Heterocycl Chem 44:983–987Google Scholar
  143. 143.
    Mo L-P, Ma Z-C, Zhang Z-H (2005) Synth Commun 35:1997–2004Google Scholar
  144. 144.
    Nagawade RR, Shinde DB (2006) Acta Chem Slov 53:210–213Google Scholar
  145. 145.
    Xia M, Wang S-H, Yuan W-B (2004) Synth Commun 34:3175–3182Google Scholar
  146. 146.
    Firouzabadi H, Iranpoor N, Jafarpour M, Ghaderi A (2006) J Mol Catal A 253:249–251Google Scholar
  147. 147.
    Reddy YT, Reddy PN, Kumar BS, Rajitha B (2005) Indian J Chem 44B:2383–2395Google Scholar
  148. 148.
    Zhang Z-H, Yin L, Wang Y-M (2005) Synthesis:1949–1954Google Scholar
  149. 149.
    Rajitha B, Reddy PN, Kumar BS, Sreenivasulu N, Reddy YRT (2005) J Chem Res:222–223Google Scholar
  150. 150.
    Lakshmi Kantam M, Aziz K, Likhar PR (2004) Catal Lett 98:117–121Google Scholar
  151. 151.
    Bandgar BP, Shaikh KA (2004) J Chem Res:34–36Google Scholar
  152. 152.
    Bartoli G, Bosco M, Foglia G, Giuliani A, Marcantoni E, Sambri L (2004) Synthesis:895–900Google Scholar
  153. 153.
    Ji S-J, Zhou M-F, Gu D-G, Wang S-Y, Loh T-P (2003) Synlett:2077–2079Google Scholar
  154. 154.
    Babu G, Srharidand N, Perumal PT (2000) Synth Commun 30:1609–1614Google Scholar
  155. 155.
    Wang L, Han J, Tian H, Sheng J, Fan Z, Tang X (2005) Synlett:337–339Google Scholar
  156. 156.
    Seyedi N, Saidi K, Khabazzadeh H (2009) Synth Commun 39:1864–1870Google Scholar
  157. 157.
    Wang S-Y, Ji S-J (2008) Synth Commun 38:1291–1298Google Scholar
  158. 158.
    Ramesh C, Ravindranath N, Das B (2003) J Chem Res Synop:72–74Google Scholar
  159. 159.
    Hosseini-Sarvani M (2008) Synth Commun 38:832–840Google Scholar
  160. 160.
    Haravi MM, Bakhtiari K, Fatehi A, Bamoharram FF (2007) Catal Commun 9:289–292Google Scholar
  161. 161.
    Azizi N, Torkian L, Saidi MR (2007) J Mol Catal A 275:109–112Google Scholar
  162. 162.
    Murugan R, Karthikeyan M, Perumal PT, Reddy BSR (2005) Tetahedron 61:12275–12281Google Scholar
  163. 163.
    Zolfigol MA, Salehi P, Shiri M (2004) Phosphorus Sulfur Silicon 179:2273–2277Google Scholar
  164. 164.
    Chakrabarty M, Ghosh N, Basak R, Harigaya Y (2002) Tetrahedron Lett 43:4075–4078Google Scholar
  165. 165.
    Banerji J, Dutta U, Basak B, Saha M, Budzikiewicz H, Chaterjee A (2001) Indian J Chem 40B:981–984Google Scholar
  166. 166.
    Karthik M, Magesh CJ, Perumal PT, Palanichamy M, Arabindoo B, Murgesan V (2005) Appl Catal A 286:137–141Google Scholar
  167. 167.
    Karthik M, Tripathi AK, Gupta NM, Palanichamy M, Murugesan V (2004) Catal Commun 5:371–375Google Scholar
  168. 168.
    Vijender Reddy A, Ravinder K, Niranjan Reddy VL, Venkateshwer GT, Ravikanth V, Venkateswarlu Y (2003) Synth Commun 33:3687–3694Google Scholar
  169. 169.
    Yadav JS, Reddy BVS, Sunitha S (2003) Adv Synth Catal 345:349–352Google Scholar
  170. 170.
    Mi X, Luo S, He J, Cheng J-P (2004) Tetrahedron Lett 45:4567–4570Google Scholar
  171. 171.
    Kundu P, Maiti G (2008) Indian J Chem 47B:1402–1406Google Scholar
  172. 172.
    Moghaddam FM, Bardajee GR, Ismaili H (2008) Asian J Chem 20:1063–1067Google Scholar
  173. 173.
    Nasreen A, Varala R, Srinivas R (2007) J Heterocycl Chem 44:983–987Google Scholar
  174. 174.
    Mohammadpoor-Baltrok I, Memarian HR, Khosropour AR, Nikoofar K (2006) Lett Org Chem 3:768–772Google Scholar
  175. 175.
    Deb ML, Bhuyan PJ (2006) Tetrahedron Lett 47:1441–1443Google Scholar
  176. 176.
    Ji S-J, Wang S-Y, Zhang Y, Loh TP (2004) Tetrahedron 60:2051–2055Google Scholar
  177. 177.
    Bandgar BP, Shaikh KA (2003) Tetrahedron Lett 44:1959–1961Google Scholar
  178. 178.
    Koshima H, Matsusaka W (2002) J Heterocycl Chem 39:1089–1091Google Scholar
  179. 179.
    Lin X-F, Cui S-L, Wang YG (2006) Synth Commun 36:3153–3160Google Scholar
  180. 180.
    Teimouri MB, Mivehchi H (2005) Synth Commun 35:1835–1843Google Scholar
  181. 181.
    Sharma GVM, Reddy JJ, Lakshmi PS, Krishna PR (2004) Tetrahedron Lett 45:7729–7732Google Scholar
  182. 182.
    Mitchell T (2005) Chem Biol Interact 156:151–153Google Scholar
  183. 183.
    Bjeldanes L (2005) Chem Biol Interact 156:155Google Scholar
  184. 184.
    Bergman J, Hogberg S, Ryhage R (1970) Tetrahedron 26:3347–3352Google Scholar
  185. 185.
    De Kruif GA, Marsman JW, Venekamp JC, Falke HE, Noordhoek J, Blauboer BJ, Wortelboer HM (1991) Chem Biol Interact 80:303–315Google Scholar
  186. 186.
    Grose KR, Bjeldanes LF (1992) Chem Res Toxicol 5:188–193Google Scholar
  187. 187.
    Riby JE, Feng C, Chang Y-C, Schaldach CM, Firestone GL, Bjeldanes LF (2000) Biochemistry 39:910–918Google Scholar
  188. 188.
    Xue L, Schaldach CM, Janosik T, Bergman J, Bjedldanes LF (2005) Chem Biol Interact 152:119–129Google Scholar
  189. 189.
    Santoso M, Somphol K, Kumar N, Black D StC (2009) Tetrahedron 65:5977–5983Google Scholar
  190. 190.
    Beldanes LF, Staub RE (2003) J Org Chem 68:167–169Google Scholar
  191. 191.
    Akgun E, Pindur U, Mueller J (1983) J Heterocycl Chem 20:1303–1305Google Scholar
  192. 192.
    Mueller J, Pfueffer L, Pindur U (1983) Monatsh Chem 116:365–370Google Scholar
  193. 193.
    Bergman J (1971) J Heterocycl Chem 20:329–330Google Scholar
  194. 194.
    Naskar S, Hazra A, Paira P, Sahu KB, Banerjee S, Mondal NB (2008) J Chem. Res:568–571Google Scholar
  195. 195.
    Zeng XF, Ji S-J, Su XM (2008) Chin J Chem 26:413–416Google Scholar
  196. 196.
    Zhang Z-H, Lin J (2007) Synth Commun 37:209–215Google Scholar
  197. 197.
    Li J, Zhou M, Li B, Zhang G (2004) Synth Commun 34:275–280Google Scholar
  198. 198.
    Chakrabarty M, Sarkar S, Linden A, Stein BW (2004) Synth Commun 34:1801–1810Google Scholar
  199. 199.
    Li J, Bing G, Wang L, Li B, Zhang G (2003) Heterocycles 60:1307–1315Google Scholar
  200. 200.
    Rameesh C, Ravindrath N, Das B (2003) J Chem Res:72–74Google Scholar
  201. 201.
    Chakrabarty M, Sarkar S (2002) Tetrahedron Lett 43:1351–1353Google Scholar
  202. 202.
    Hazra A, Paira P, Sahu KB, Banerjee S, Mondal NB (2008) Catal Commun 9:1681–1684Google Scholar
  203. 203.
    Szmuszkovicz J (1957) J Am Chem Soc 79:2819–2821Google Scholar
  204. 204.
    Noland WE, Christensen GM, Sauer GL, Dutton GGS (1955) J Am Chem Soc 77:456–457Google Scholar
  205. 205.
    Bandini M, Melloni A, Tommasi S, Umani-Ronchi A (2005) Synlett:1199–1222Google Scholar
  206. 206.
    Zhang H-B, Liu L, Liu Y-L, Chen YJ, Wang J, Wang D (2007) Synth Commun 37:173–181Google Scholar
  207. 207.
    Ekbote SS, Panda AG, Bhor MD, Bhanage BH (2009) Catal Commun 10:1569–1573Google Scholar
  208. 208.
    Bandini M, Fagioli M, Umani-Ronchi A (2004) Adv Synth Catal 346:545–548Google Scholar
  209. 209.
    Das B, Chowdhury N, Damodar K, Reddy KR (2007) Helv Chim Acta 90:340–345Google Scholar
  210. 210.
    Harrington PE, Kerr MA (1996) Synlett:1047–1048Google Scholar
  211. 211.
    Yadav JS, Abraham S, Reddy BVS, Sabitha G (2001) Synthesis:2165–2169Google Scholar
  212. 212.
    Maiti G, Kundu P (2007) Synth Commun 37:2309–2316Google Scholar
  213. 213.
    Nayak S (2006) Synth Commun 36:1307–1315Google Scholar
  214. 214.
    Xu R, Ding JC, Chen XA, Liu MC, Wu HY (2009) Chin Chem Lett 20:676–679Google Scholar
  215. 215.
    Bandini M, Cozzi PG, Giacomini M, Melchiorre P, Selva S, Umani-Ronchi A (2002) J Org Chem 67:3700–3704Google Scholar
  216. 216.
    Huang Z-H, Zou J-P, Jiang W-Q (2006) Tetrahedron Lett 47:7965–7968Google Scholar
  217. 217.
    Sun L, Gao C, Zhou W, Wei Y (2008) Indian J Chem 47B:481–484Google Scholar
  218. 218.
    Srivastava N, Banik BK (2003) J Org Chem 68:2109–2114Google Scholar
  219. 219.
    Alam MM, Varala R, Adapa SR (2003) Tetrahedron Lett 44:5115–5119Google Scholar
  220. 220.
    Firouzabadi H, Iranpoor N, Jafrapour M, Ghaderi A (2006) J Mol Catal C 252:150–155Google Scholar
  221. 221.
    Tahir R, Banert K, Sebti S (2006) Appl Catal A 315:147–149Google Scholar
  222. 222.
    Poupaert JH, Bukuru J, Gozzo A (1999) Monatsh Chem 130:929–932Google Scholar
  223. 223.
    Singh DU, Singh PR, Samant SD (2006) Synth Commun 36:1265–1271Google Scholar
  224. 224.
    Shi M, Cui S-C, Li Q-J (2004) Tetrahedron 60:6679–6684Google Scholar
  225. 225.
    Li DP, Guo Y-C, Ding Y, Xiao W-J (2006) Chem Commun:799–801Google Scholar
  226. 226.
    Wang S-Y, Ji S-J, Loh T-P (2003) Synlett:2377–2379Google Scholar
  227. 227.
    Banik BK, Fernandez M, Alvarez C (2005) Tetrahedron Lett 46:2479–2482Google Scholar
  228. 228.
    Bartoli G, Bartolacci M, Bosco M, Foglia G, Giuliani A, Marcantoni E, Sambri L, Torregiani E (2003) J Org Chem 68:4594–4597Google Scholar
  229. 229.
    Ko S, Lin C, Tu Z, Wang Y-F, Wang C-C, Yao C-F (2006) Tetrahedron Lett 47:487–492Google Scholar
  230. 230.
    Wu GL, Wu LM (2008) Chin Chem Lett 19:55–58Google Scholar
  231. 231.
    Gu D, Ji S, Wang H, Xu Q (2008) Synth Commun 38:1212–1223Google Scholar
  232. 232.
    Yu C-J, Lin C-J (2009) Molecules 14:3222–3228Google Scholar
  233. 233.
    Gu Y, Ogawa C, Kobayashi S (2007) Org Lett 9:175–178Google Scholar
  234. 234.
    Hagiwara H, Sekifuji M, Hoshi T, Suzuki T, Quanxi B, Qiao K, Yokoyama C (2008) Synlett:608–610Google Scholar
  235. 235.
    Zhou W, Xu L-W, Li L, Yang L, Xia C-G (2006) Eur J Org Chem:5223–5227Google Scholar
  236. 236.
    Itoh T, Uehara H, Ogiso K, Nomura S, Hayase S, Kawatsura M (2007) Chem Lett 36:50–51Google Scholar
  237. 237.
    Yadav JS, Reddy BVS, Baishya G, Reddy KV, Narsaiah AV (2005) Tetrahedron 61:9541–9544Google Scholar
  238. 238.
    Liu X, Cui S, Wang Y (2006) Lett Org Chem 3:414–418Google Scholar
  239. 239.
    Ji S-J, Wang S-Y (2005) Ultrason Sonochem 12:339–343Google Scholar
  240. 240.
    Zeng X-F, Ji S-J, Shen S-S (2007) Chin J Chem 25:1777–1780Google Scholar
  241. 241.
    Ji S-J, Wang S-Y (2003) Synlett:2074–2076Google Scholar
  242. 242.
    Zhan Z-P, Lang K (2005) Synlett:1551–1554Google Scholar
  243. 243.
    Scretti A, Villano R, Acocello MR (2009) Molecules 14:3030–3036Google Scholar
  244. 244.
    Blay G, Fernandez I, Pedro JR, Vila C (2007) Org Lett 9:2601–2604Google Scholar
  245. 245.
    Bandini M, Fagioli M, Melchiorre B, Melloni A, Umani-Ronchi A (2003) Tetrahedron Lett 44:5843–5846Google Scholar
  246. 246.
    Bandini M, Fagioli M, Garavelli M, Melloni A, Trigari V, Umani-Ronchi A (2004) J Org Chem 69:7511–7518Google Scholar
  247. 247.
    Adachi S, Tanaka F, Watanabe K, Harada T (2009) Org Lett 11:5206–5209Google Scholar
  248. 248.
    Palomo C, Oiarbide M, Kardak BG, Garcia JM, Linden A (2005) J Am Chem Soc 125:4154–4155Google Scholar
  249. 249.
    Yang H, Hong Y-T, Kim S (2007) Org Lett 9:2281–2284Google Scholar
  250. 250.
    Evans DA, Scheidt KA, Fandrick KR, Lam HW, Wu J (2003) J Am Chem Soc 125:10780–10781Google Scholar
  251. 251.
    Evans DA, Fandrick KR, Song H-J, Scheidt KA, Xu R (2007) J Am Chem Soc 129:10029–10041Google Scholar
  252. 252.
    Austin JF, MacMillan DWC (2002) J Am Chem Soc 124:1172–1173Google Scholar
  253. 253.
    King HD, Meng Z, Denhart D, Mattson R, Kimura R, Wu D, Gao Q, Macor JE (2005) Org Lett 7:3427–3440Google Scholar
  254. 254.
    Chen W, Du W, Yue L, Li R, Wu Y, Ding L-S, Chen Y-C (2007) Org Biomol Chem 5:816–821Google Scholar
  255. 255.
    Bartoli G, Bosco M, Carlone A, Pesciaioli F, Sambri L, Melchiorre P (2007) Org Lett 9:1403–1405Google Scholar
  256. 256.
    Blay G, Fernandez I, Monleon A, Pedro JR, Vila C (2009) Tetrahedron 65:9264–9270Google Scholar
  257. 257.
    Silvanus AC, Heffernan SJ, Liptrot DJ, Kociock-Kohn G, Andrews BI, Carbery DR (2009) Org Lett 11:1175–1178Google Scholar
  258. 258.
    Li J-T, Lin Z-P (2008) Asian J Chem 20:1109–1120Google Scholar
  259. 259.
    Li J-T, Lin ZP, Liu C-T (2008) Indian J Chem 47B:283–290Google Scholar
  260. 260.
    Tabatabaeian K, Mamaghani M, Mahmoodi NO, Khorshidi A (2007) J Mol Catal A 270:112–116Google Scholar
  261. 261.
    Bandini M, Fagioli M, Melloni A, Umani-Ronchi A (2003) Synthesis:397–402Google Scholar
  262. 262.
    Zhuang W, Hansen T, Jorgensen KA (2001) Chem Commun:347–348Google Scholar
  263. 263.
    Zhou J, Tang Y (2002) J Am Chem Soc 124:9030–9031Google Scholar
  264. 264.
    Noland WE, Hartman PJ, Am J (1954) Chem Soc 76:3227–3228Google Scholar
  265. 265.
    Noland WE, Hovden RA (1959) J Org Chem 24:894–895Google Scholar
  266. 266.
    Ranganathan D, Rao CB, Ranganathan S, Mehrotra AK, Iyengar R (1980) J Org Chem 45:1185–1189Google Scholar
  267. 267.
    Kusurkar RS, Alkobati NAH, Gokule AS, Chaudhari PM, Waghchaure PB (2006) Synth Commun 36:1075–1081Google Scholar
  268. 268.
    Habib PM, Kuvalce V, Ku C-W, Yao CF (2008) Tetrahedron Lett 49:7005–7007Google Scholar
  269. 269.
    Finouzabasi H, Iranpoor N, Nowouzi F (2005) Chem Commun:789–791Google Scholar
  270. 270.
    Manabe K, Aoyama N, Kobayahsi S (2001) Adv Synth Catal 343:174–176Google Scholar
  271. 271.
    Komoto I, Kobayashi S (2002) Org Lett 4:1115–1118Google Scholar
  272. 272.
    Azizi N, Arynasab F, Saidi MR (2006) Org Biomol Chem 4:4275–4277Google Scholar
  273. 273.
    Harri GS, Nagaraju M, Murthy MM (2008) Synth Commun 38:100–105Google Scholar
  274. 274.
    An L-T, Zou J-P, Zhang L-L, Zhang Y (2007) Tetrahedron Lett 48:4297–4300Google Scholar
  275. 275.
    Bandini M, Melchiorre P, Melloni A, Umani-Ronchi A (2002) Synthesis:1110–1114Google Scholar
  276. 276.
    Zhan Z-P, Yang R-F, Lang K (2005) Tetrahedron Lett 46:3859–3862Google Scholar
  277. 277.
    Meshram HM, Kumar DA, Reddy BC (2009) Helv Chim Acta 92:1002–1006Google Scholar
  278. 278.
    Bartoli G, Di Antonio G, Giuli S, Marcantoni E, Marcolini M, Paoletti M (2008) Synthesis:320–324Google Scholar
  279. 279.
    Kuo C-W, Wang C-C, Fang H-L, Raju BR, Kavala V, Habib PM, Yao C-F (2009) Molecules 14:3952–3963Google Scholar
  280. 280.
    Lin C, Hsu J, Sastry MNV, Fang H, Tu Z, Liu J-T, Ching-Fa Y (2005) Tetrahedron 61:11751–11757Google Scholar
  281. 281.
    Singh PK, Bisai A, Singh VK (2007) Tetrahedron Lett 48:1127–1129Google Scholar
  282. 282.
    Jiu Y-X, Zhu S-F, Yang Y, Zhou Q-C (2006) J Org Chem 71:75–80Google Scholar
  283. 283.
    Lu S-F, Du D-M, Xu J (2006) Org Lett 8:2115–2118Google Scholar
  284. 284.
    McKeon SC, Muller-Bunz H, Guiry PJ (2009) Eur J Org Chem:4833–4841Google Scholar
  285. 285.
    Yokoyama N, Arai T (2009) Chem Commun:3285–3287Google Scholar
  286. 286.
    Zhuang W, Hazell RG, Jorgensen KA (2005) Org Biomol Chem 3:2566–2571Google Scholar
  287. 287.
    Fleming EM, McCabe T, Connon SJ (2006) Tetrahedron Lett 47:7037–7042Google Scholar
  288. 288.
    Yuan ZL, Lei ZY, Shi M (2008) Tetrahedron Asymmetry 19:1339–1346Google Scholar
  289. 289.
    Herrera RP, Sgarzani V, Bernardi L, Ricci A (2005) Angew Chem Int Ed 44:6576–6579Google Scholar
  290. 290.
    Ganesh M, Seidel D (2008) J Am Chem Soc 130:1464–1645Google Scholar
  291. 291.
    Itoh J, Fuchibe K, Akiyama T (2008) Angew Chem Int Ed 47:4016–4018Google Scholar
  292. 292.
    Angelini E, Balsamini C, Bartoccini F, Lucarini S, Piersanti G (2008) J Org Chem 73:5654–5657Google Scholar
  293. 293.
    Guo Q-X, Peng Y-G, Zhang J-W, Song L, Feng Z, Gong L-Z (2009) Org Lett 11:4620–4623Google Scholar
  294. 294.
    Agnusdei M, Bandini M, Melloni A, Umani-Ronchi A (2003) J Org Chem 68:7126–7129Google Scholar
  295. 295.
    Cai Q, Zhao Z-A, You S-L (2009) Angew Chem Int Ed 48:7428–7431Google Scholar
  296. 296.
    Li C-F, Liu H, Liao J, Cao Y-J, Liu X-P, Xiao W-J (2007) Org Lett 9:1847–1850Google Scholar
  297. 297.
    Zhou JL, Ye MC, Sun X-L, Tang Y (2009) Tetrahedron 65:6877–6881Google Scholar
  298. 298.
    Heureux N, Wouters J, Marko IE (2005) Org Lett 7:5245–5248Google Scholar
  299. 299.
    Austin JF, Kim S-G, Sinz CJ, Xiao W-J, MacMillan DWC (2004) Proc Natl Acad Sci USA 101:5482–5487Google Scholar
  300. 300.
    Kuhn H, Stein O (1937) Ber Deutsch Chem Gesell 70:567–569Google Scholar
  301. 301.
    Swaminathan S, Narasimhan K (1966) Chem Ber 99:889–894Google Scholar
  302. 302.
    Sharifi A, Mirzaei M, Naimi-Jamal MR (2001) Monatsh Chem 132:875–880Google Scholar
  303. 303.
    Grumbach H-J, Arend M, Risch N (1996) Synthesis:833–887Google Scholar
  304. 304.
    Xie W, Bloomfiled KM, Jin Y, Dolney NY, Wang PG (1999) Synlett:498–500Google Scholar
  305. 305.
    Janczuk A, Zhang W, Xie W, Lou S, Cheng J-P, Wang PG (2002) Tetrahedron Lett 43:4271–4274Google Scholar
  306. 306.
    Katritzky AR, Yang Z, Lam JN (1992) Tetrahedron 48:4971–4978Google Scholar
  307. 307.
    Love BE, Nguyen BT (1998) Synlett:1123–1125Google Scholar
  308. 308.
    Mao H, Wang X, Wang W, He L, Kong L, Liu J (1998) Synthesis:2582–2588Google Scholar
  309. 309.
    Jia Y-X, Xie J-H, Duan H-F, Wang L-X, Zhou Q-L (2006) Org Lett 8:1621–1624Google Scholar
  310. 310.
    Wang Y-Q, Song J, Hong R, Li H, Deng L (2006) J Am Chem Soc 128:8156–8157Google Scholar
  311. 311.
    Kang Q, Zhao Z-A, You S-L (2007) J Am Chem Soc 129:1484–1485Google Scholar
  312. 312.
    Liu Z, Shi M (2009) Tetrahedron Asymmetry 20:119–121Google Scholar
  313. 313.
    Abid M, Teixeira L, Torok B (2008) Org Lett 10:933–935Google Scholar
  314. 314.
    Jia Y-X, Zhong J, Zhu S-F, Zhang C-M, Zhu Q-L (2007) Angew Chem Int Ed Engl 48:5565–5567Google Scholar
  315. 315.
    Cox ED, Cook JM (1995) Chem Rev 95:1797–1842Google Scholar
  316. 316.
    Ungemach F, Cook JM (1978) Heterocycles 8:1089–1119Google Scholar
  317. 317.
    Jackson AH, Smith P (1968) Tetrahedron 24:2227–2239Google Scholar
  318. 318.
    Kawate T, Nagawa M, Ogata K, Hino T (1992) Heterocycles 33:801–811Google Scholar
  319. 319.
    Kusurkur RS, Alkobati NAH, Gokule AS, Puranik VG (2008) Tetrahedron 64:1654–1662Google Scholar
  320. 320.
    Kuo F-M, Tseng M-C, Yen Y-H, Chu Y-H (2004) Tetrahedron 60:12075–12084Google Scholar
  321. 321.
    Tsuji R, Yamanaka M, Nishida A, Nakagawa M (2002) Chem Lett:428–429Google Scholar
  322. 322.
    Zhou H, Han D, Liao X, Cook JM (2005) Tetrahedron Lett 46:4219–4224Google Scholar
  323. 323.
    Yu J, Wearing X, Cook JM (2005) J Org Chem 70:3963–3979Google Scholar
  324. 324.
    Zhao H, Liao X, Cook JM (2004) Org Lett 6:249–252Google Scholar
  325. 325.
    Zhao S, Liao X, Wang T, Flippen-Anderson J, Cook JM (2003) J Org Chem 68:6279–6295Google Scholar
  326. 326.
    Yu J, Wang T, Liu X, Deschamps J, Flippen-Anderson J, Liao X, Cook JM (2003) J Org Chem 68:7565–7581Google Scholar
  327. 327.
    Kumpaty HJ, Van Linn ML, Kabir MS, Forsterling FH, Deschamps JR, Cook JM (2009) J Org Chem 74:2771–2779Google Scholar
  328. 328.
    Ma J, Yin W, Zhou H, Liao X, Cook JM (2009) J Org Chem 74:264–273Google Scholar
  329. 329.
    Zhou H, Liao X, Yin W, Ma J, Cook JM (2006) J Org Chem 71:251–259Google Scholar
  330. 330.
    Bailey PD, Hollinshead SP, McLay NR, Morgan K, Palmer SJ, Prince SN, Reynolds CD, Wood SD (1993) J Chem Soc Perkin Trans 1:431–439Google Scholar
  331. 331.
    Bailey PD, Collier ID, Hollinshead SP, Moore MH, Morgan KM, Smith DI, Vernon JM (1997) J Chem Soc Perkin Trans 1:1209–1214Google Scholar
  332. 332.
    Bailey PD, Morgan KM (2000) J Chem Soc Perkin Trans 1:3578–3583Google Scholar
  333. 333.
    Bailey PD, Morgan KM, Smith DI, Vernon JM (2000) J Chem Soc Perkin Trans 1:3566–3577Google Scholar
  334. 334.
    Bailey PD, Cochrane PJ, Lorenz K, Collier ID, Pearson DPJ, Rosair GM (2001) Tetrahedron Lett 42:113–115Google Scholar
  335. 335.
    Lewis SE (2006) Tetrahedron 62:8655–8681Google Scholar
  336. 336.
    Waldmann H, Schmidt C, Jansen M, Geb J (1994) Tetrahedron 50:11865–11884Google Scholar
  337. 337.
    Soe T, Kawate T, Fukui N, Hino T, Nakagawa M (1996) Heterocycles 42:347–358Google Scholar
  338. 338.
    Kawate T, Yamanaka M, Nakagawa M (1999) Hetereocycles 50:1033–1039Google Scholar
  339. 339.
    Wee AGH, Yu Q (2001) J Org Chem 66:8935–8943Google Scholar
  340. 340.
    Schultz AG, Pettus L, Org J (1997) Chem 62:6855–6861Google Scholar
  341. 341.
    Taylor MS, Jacobsen EN (2004) J Am Chem Soc 126:10558–10559Google Scholar
  342. 342.
    Raheem IT, Thiara PS, Peterson EA, Jacobsen EN (2007) J Am Chem Soc 129:13404–13405Google Scholar
  343. 343.
    Mergott DJ, Zuend SJ, Jacobsen EN (2005) Org Lett 10:745–748Google Scholar
  344. 344.
    Seayad J, Seayad AM, List B (2006) J Am Chem Soc 128:1086–1087Google Scholar
  345. 345.
    Sewogbind NV, Wanner MJ, Ingemann S, de Gelder R, van Maarseveen HH, Heimstra H (2008) J Org Chem 73:6405–6408Google Scholar
  346. 346.
    Wanner MJ, Boots RNA, Eradus B, de Gelder R, van Maarseveen JH, Heimstra H (2009) Org Lett 11:2579–2581Google Scholar
  347. 347.
    Yamada H, Kawate T, Matsumizu M, Nishida A, Yamaguchi K, Nakagawa M (1998) J Org Chem 63:6348–6354Google Scholar
  348. 348.
    Narayanan K, Schindler L, Cook JM (1991) J Org Chem 56:359–365Google Scholar
  349. 349.
    Amann R, Arnold K, Spitzner D, Majer Z, Snatzke G (1996) Liegigs Ann:349–355Google Scholar
  350. 350.
    Fontaine H, Baussanne I, Royer J (1997) Synth Commun 27:2817–2824Google Scholar
  351. 351.
    Ghosh AK, Kawahama R (2000) J Org Chem 65:5433–5434Google Scholar
  352. 352.
    Liu H, Doemling A (2009) J Org Chem 74:6895–6898Google Scholar
  353. 353.
    Connors RV, Zhang AJ, Shuttleworth SJ (2002) Tetrahedron Lett 43:6661–6663Google Scholar
  354. 354.
    Wu TYH, Schultz PG (2002) Org Lett 4:4033–4036Google Scholar
  355. 355.
    Nielsen TE, Meldal M (2004) J Org Chem 69:3765–3773Google Scholar
  356. 356.
    Agarwal PK, Sawant D, Sharma S, Kundu B (2009) Eur J Org Chem:292–303Google Scholar
  357. 357.
    Oudin A, Courtois M, Rideau M, Clastre M (2007) Phytochem Rev 6:259–276Google Scholar
  358. 358.
    Hedhili S, Courdavault V, Giglioli-Guivarc’h N, Gantet P (2007) Phytochem Rev 6:341–351Google Scholar
  359. 359.
    Ma X, Panjikar S, Koepke J, Loris E, Stockigt J (2006) Plant Cell 18:907–920Google Scholar
  360. 360.
    Loris EA, Panjikar S, Ruppert M, Barleben L, Unger M, Schubel U, Stockigt J (2007) Chem Biol 14:979–985Google Scholar
  361. 361.
    Maresh JJ, Giddings L-A, Friedrich A, Loris EA, Panjikar S, Trout BL, Stockigt J, Peters B, O’Connor SE (2008) J Am Chem Soc 130:710–723Google Scholar
  362. 362.
    Salame R, Gravel E, Leblanc K, Poupon E (2009) Org Lett 11:1891–1894Google Scholar
  363. 363.
    Pal B, Jaisankar P, Giri VS (2003) Synth Commun 33:2339–2348Google Scholar
  364. 364.
    Aube J, Ghosh S, Tanol M (1994) J Am Chem Soc 116:9009–9018Google Scholar
  365. 365.
    Desmaele D, Mekouar K, d’Angelo J (1997) J Org Chem 62:3890–3901Google Scholar
  366. 366.
    Jones G, Stanforth SP (1997) Org React 49:1–330Google Scholar
  367. 367.
    Black DStC (1998) Adv Nitrogen Heterocycl 3:85–116Google Scholar
  368. 368.
    James PN, Snyder HR (1963) Org Synth Coll 4:539–542Google Scholar
  369. 369.
    Watson TJN, Horgan SW, Shah RS, Farr RA, Schnettler RA, Nevill CR Jr, Weiberth FJ, Huber EW, Baron BM, Webster ME, Mishra RK, Harrison BL, Nyce PL, Rand CL, Goralski CT (2000) Org Process Res Dev 4:477–487Google Scholar
  370. 370.
    Condie GC, Channon MF, Ivory AJ, Kumar N, Black DStC (2005) Tetrahedron 61:4989–5004Google Scholar
  371. 371.
    Chatterjee A, Biswas KM (1973) J Org Chem 38:4002–4003Google Scholar
  372. 372.
    Tois J, Franzen R, Aito O, Laakso I, Kylanlahti I (2001) J Comb Chem 3:542–545Google Scholar
  373. 373.
    Saxton JE (1952) J Chem Soc:3592–3594Google Scholar
  374. 374.
    Slaett J, Romero I, Bergman J (2004) Synthesis:2760–2765Google Scholar
  375. 375.
    Speeter ME, Anthony WC (1954) J Am Chem Soc 76:6208–6210Google Scholar
  376. 376.
    Brandt SD, Tirunarayanapuram SS, Freeman S, Dempster N, Barker SA, Daley PF, Cozzi NV, Martins CPB (2008) J Label Compd Radiopharm 51:423–429Google Scholar
  377. 377.
    Collins I, Davey WB, Rowley M, Quirk K, Bromidge FA, McKernan RM, Thompson S-A, Wafford KA (2000) Bioorg Med Chem Lett 10:1381–1384Google Scholar
  378. 378.
    Primofiori G, Da Settimo F, Taliani S, Simorini F, Patrizi MP, Novellino E, Greco G, Abignente E, Costa B, Chelli B, Martini C (2004) J Med Chem 47:1852–1855Google Scholar
  379. 379.
    Primofiore G, Da Settimo F, Marini AM, Taliani S, La Motta C, Simorini F, Novellino E, Greco G, Cosimelli B, Ehlardo M, Sala A, Besnard F, Montali M, Martini C (2006) J Med Chem 49:2489–2495Google Scholar
  380. 380.
    Homes TP, Mattner F, Keller PA, Katsifis A (2006) Bioorg Med Chem 14:3938–3946Google Scholar
  381. 381.
    Taliani S, Simorini F, Sergianni V, La Motta C, Da Settimo F, Cosimelli B, Abignente E, Greco G, Novellino E, Rossi L, Gremigni V, Spinetti F, Chelli B, Martini C (2007) J Med Chem 30:404–407Google Scholar
  382. 382.
    Primofiore G, Taliani S, Da Settimo F, Marini AM, La Motta C, Simorini F, Patrizi MP, Sergianni V, Novellino E, Greco G, Cosimelli B, Calderone V, Montali M, Besnard F, Martini C (2007) J Med Chem 50:1627–1634Google Scholar
  383. 383.
    Da Settimo F, Simorini F, Taliani S, La Motta C, Marini AM, Salerno S, Bellandi M, Novellino E, Greco G, Cosimelli B, Da Pozzo E, Costa B, Simola N, Morelli M, Martini C (2008) J Med Chem 51:5798–5806Google Scholar
  384. 384.
    Taliani S, Cosimelli B, Da Settimo F, Marini AM, La Motta C, Simorini F, Salerno S, Novellino E, Greco G, Cosconati S, Marinelli L, Salvetti F, L’Abbate G, Trasciatti S, Maontali M, Costa B, Martini C (2009) J Med Chem 52:3724–3734Google Scholar
  385. 385.
    Meanwell NA, Wallace OB, Wang H, Deshpande M, Pearce BC, Trehan A, Yeung K-S, Qui Z, Wright JJK, Robinson BA, Gong Y-F, Wang H-GH, Blair WS, Shi P-Y, Lin P (2009) Bioorg Med Chem Lett 19:5136–5139Google Scholar
  386. 386.
    Wang T, Kadow JF, Zhang Z, Yin Z, Gao Q, Wu D, Parker DD, Yang Z, Zadjura L, Robinson BA, Gong Y-F, Blair WS, Shi P-Y, Yamanaka G, Lin P-F, Meanwell NA (2009) Bioorg Med Chem Lett 19:5140–5145Google Scholar
  387. 387.
    Takhni M, Singh G, Murugan C, Thaplyyal N, Maitra S, Bhaskarreddy KM, Amarnath PVS, Mallik A, Harisudan T, Trivedi RK, Sreenivas K, Selvakumar N, Iqbal J (2008) Bioorg Med Chem Lett 18:5150–5185Google Scholar
  388. 388.
    Katritzky AR, Jiang R, Suzuki K (2005) J Org Chem 70:4993–5000Google Scholar
  389. 389.
    Dempoulos VJ, Nicolaou I (1998) Synthesis:1519–1522Google Scholar
  390. 390.
    Cui D-M, Kawamura M, Shimada S, Hayashi T, Tanaka M (2003) Tetrahedron Lett 44:4007–4010Google Scholar
  391. 391.
    Cui D-M, Zhang C, Kawamura M, Shimada S (2004) Tetrahedron Lett 45:1741–1745Google Scholar
  392. 392.
    Somei M, Yokoyama Y, Murakami Y, Ninomiya I, Kiguchi T, Naito T (2000) Alkaloids 54:191–257Google Scholar
  393. 393.
    Kurokawa M, Watanabe T, Ishikawa T (2007) Helv Chim Acta 90:574–586Google Scholar
  394. 394.
    Spandoni G, Balsami C, Diamantini G, Di Giacomo B, Tarzia G, Mor M, Plazzi PV, Rivara S, Luccini V, Nonno R, Pannacci M, Fraschini F, Stankov BM (1997) J Med Chem 40:1990–2002Google Scholar
  395. 395.
    Fillion E, Dumas AM (2008) J Org Chem 73:2920–2923Google Scholar
  396. 396.
    Fillion E, Fishlock D, Wilsily A, Goll JM (2005) J Org Chem 70:1316–1327Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of VirginiaCharlottesvilleUSA

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