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Complexity via Gold-Catalyzed Molecular Gymnastics

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Abstract

Reactions of 1,6-enynes catalyzed by gold(I) complexes usually proceed stereospecifically through highly distorted cyclopropyl gold carbenes. Substrates with an alkoxy substituent at the propargylic position undergo stereoselective transformations through intermediates in which the OR group and the gold carbene are anti-oriented. Intramolecular attack of carbonyl groups to the cyclopropyl gold carbene is faster than the 1,5-migration of the OR groups, which itself is faster than the intramolecular cyclopropanation by a pendant alkenyl group. The intramolecular attack of carbonyl groups is the key transformation in the [2+2+2] gold-catalyzed cycloaddition, which has been applied in the total synthesis of (+)-orientalol F.

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References

  1. Jiménez-Núñez E, Echavarren AM (2008) Chem Rev 108:3326–3350

    Article  CAS  Google Scholar 

  2. Gorin DJ, Sherry BD, Toste FD (2008) Chem Rev 108:3351–3378

    Article  CAS  Google Scholar 

  3. Michelet V, Toullec PY, Genêt JP (2008) Angew Chem Int Ed 47:4268–4315

    Article  CAS  Google Scholar 

  4. Fürstner A (2009) Chem Soc Rev 38:3208–3221

    Article  CAS  Google Scholar 

  5. Nieto-Oberhuber C, Muñoz MP, Buñuel E, Nevado C, Cárdenas DJ, Echavarren AM (2004) Angew Chem Int Ed 43:2402–2406

    Article  CAS  Google Scholar 

  6. Nieto-Oberhuber C, Muñoz MP, López S, Jiménez-Núñez E, Nevado C, Herrero-Gómez E, Raducan M, Echavarren AM (2006) Chem Eur J 12:1677–1693

    Article  CAS  Google Scholar 

  7. Ferrer C, Raducan M, Nevado C, Claverie CK, Echavarren AM (2007) Tetrahedron 63:6306–6316

    Article  CAS  Google Scholar 

  8. Nevado C, Cárdenas DJ, Echavarren AM (2003) Chem Eur J 9:2627–2635

    Article  CAS  Google Scholar 

  9. Zhang L, Kozmin SA (2005) J Am Chem Soc 127:6962–6963

    Article  CAS  Google Scholar 

  10. Buzas AK, Istrate FM, Gagosz F (2007) Angew Chem Int Ed 46:1141–1144

    Article  CAS  Google Scholar 

  11. Sherry BD, Maus L, Laforteza BN, Toste FD (2006) J Am Chem Soc 128:8132–8133

    Article  CAS  Google Scholar 

  12. Park S, Lee D (2006) J Am Chem Soc 128:10664–10665

    Article  CAS  Google Scholar 

  13. Horino Y, Luzung MR, Toste FD (2006) J Am Chem Soc 128:11364–11365

    Article  CAS  Google Scholar 

  14. Witham CA, Mauleón P, Shapiro ND, Sherry BD, Toste FD (2007) J Am Chem Soc 129:5838–5839

    Article  CAS  Google Scholar 

  15. Nieto-Oberhuber C, López S, Echavarren AM (2005) J Am Chem Soc 127:6178–6179

    Article  CAS  Google Scholar 

  16. Nieto-Oberhuber C, Pérez-Galán P, Herrero-Gómez E, Lauterbach T, Rodríguez C, López S, Bour C, Rosellón A, Cárdenas DJ, Echavarren AM (2008) J Am Chem Soc 130:269–279

    Article  CAS  Google Scholar 

  17. Trost BM, Tanoury GJ (1988) J Am Chem Soc 110:1636–1638

    Article  CAS  Google Scholar 

  18. Trost BM, Trost MK (1991) Tetrahedron Lett 32:3647–3650

    Article  CAS  Google Scholar 

  19. Trost BM, Doherty GA (2000) J Am Chem Soc 122:3801–3810

    Article  CAS  Google Scholar 

  20. Trost BM, Yanai M, Hoogsteed K (1993) J Am Chem Soc 115:5294–5295

    Article  CAS  Google Scholar 

  21. Lee SI, Chatani N (2009) Chem Commun 371–384

  22. Chatani N, Morimoto T, Muto T, Murai S (1994) J Am Chem Soc 116:6049–6050

    Article  CAS  Google Scholar 

  23. Chatani N, Furukawa N, Sakurai H, Murai S (1996) Organometallics 15:901–903

    Article  CAS  Google Scholar 

  24. Chatani N, Inoue H, Morimoto T, Muto T, Murai S (2001) J Org Chem 66:4433–4436

    Article  CAS  Google Scholar 

  25. Chatani N, Inoue H, Kotsuma T, Murai S (2002) J Am Chem Soc 124:10294–10295

    Article  CAS  Google Scholar 

  26. Miyanohana Y, Inoue, Chatani HN (2004) J Org Chem 69:8541–8543

    Article  CAS  Google Scholar 

  27. Miyanohana Y, Chatani N (2006) Org Lett 8:2155–2158

    Article  CAS  Google Scholar 

  28. Nakai H, Chatani N (2007) Chem Lett 1494–1495

  29. Fürstner A, Szillat H, Stelzer F (2000) J Am Chem Soc 122:6785–6786

    Article  CAS  Google Scholar 

  30. Fürstner A, Stelzer F, Szillat H (2001) J Am Chem Soc 123:11863–11869

    Article  CAS  Google Scholar 

  31. Fürstner A, Szillat H, Gabor B, Mynott R (1998) J Am Chem Soc 120:8305–8314

    Article  Google Scholar 

  32. Oi S, Tsukamoto I, Miyano S, Inoue Y (2001) Organometallics 20:3704–3709

    Article  CAS  Google Scholar 

  33. Oh CH, Bang SY, Rhim CY (2003) Bull Korean Chem Soc 24:887–888

    Article  CAS  Google Scholar 

  34. Bajracharya GB, Nakamura I, Yamamoto Y (2005) J Org Chem 70:892–897

    Article  CAS  Google Scholar 

  35. Méndez M, Muñoz MP, Echavarren AM (2000) J Am Chem Soc 122:11549–11550

    Article  CAS  Google Scholar 

  36. Méndez M, Muñoz MP, Nevado C, Cárdenas DJ, Echavarren AM (2001) J Am Chem Soc 123:10511–10520

    Article  CAS  Google Scholar 

  37. Kim SM, Lee SI, Chung YK (2006) Org Lett 8:5425–5427

    Article  CAS  Google Scholar 

  38. Cabello N, Jiménez-Núñez E, Buñuel E, Cárdenas DJ, Echavarren AM (2007) Eur J Org Chem 4217–4223

  39. Faller JW, Fontaine PP (2006) J Organomet Chem 691:1912

    Article  CAS  Google Scholar 

  40. Lee SI, Kim SM, Choi MR, Kim SY, Chung YK (2006) J Org Chem 71:9366–9372

    Article  CAS  Google Scholar 

  41. Fürstner A, Schlecker A, Lehmann CW (2007) Chem Commun 4277–4279

  42. Böhringer S, Gagosz F (2008) Adv Synth Catal 350:2617–2630

    Article  CAS  Google Scholar 

  43. Buzas A, Istrate F, Le Goff XF, Odabachian Y, Gagosz F (2009) J Organomet Chem 694:515–519

    Article  CAS  Google Scholar 

  44. Fürstner A, Davies PW, Gress T (2005) J Am Chem Soc 127:8244–8245

    Article  CAS  Google Scholar 

  45. Marion F, Coulomb J, Courillon C, Fernsternbank L, Malacria M (2004) Org Lett 6:1509–1511

    Article  CAS  Google Scholar 

  46. Couty S, Meyer C, Cossy J (2006) Angew Chem Int Ed 45:6726–6730

    Article  CAS  Google Scholar 

  47. Couty S, Meyer C, Cossy J (2009) Tetrahedron 65:1809–1832

    Article  CAS  Google Scholar 

  48. Diver ST, Giessert AJ (2004) Chem Rev 104:1317–1382

    Article  CAS  Google Scholar 

  49. Mori M (2007) Adv Synth Catal 349:121–135

    Article  CAS  Google Scholar 

  50. Nieto-Oberhuber C, López S, Jiménez-Núñez E, Echavarren AM (2006) Chem Eur J 11:5916–5923

    Article  CAS  Google Scholar 

  51. Soriano E, Marco-Contelles J (2009) Acc Chem Res 42:1026–1036

    Article  CAS  Google Scholar 

  52. Nieto-Oberhuber C, López S, Muñoz MP, Cárdenas DJ, Buñuel E, Nevado C, Echavarren AM (2005) Angew Chem Int Ed 44:6146–6148

    Article  CAS  Google Scholar 

  53. Ota K, Chatani N (2008) Chem Commun 2906–2907

  54. Ota K, Ick Lee S, Tang J-M, Takachi M, Nakai H, Morimoto T, Sakurai H, Kataoka K, Chatani N (2009) J Am Chem Soc 131:15203–15211

    Article  CAS  Google Scholar 

  55. López S, Herrero-Gómez E, Pérez-Galán P, Nieto-Oberhuber C, Echavarren AM (2006) Angew Chem Int Ed 45:6029–6032

    Article  CAS  Google Scholar 

  56. Toullec PY, Genin E, Leseurre L, Genêt J-P, Michelet V (2006) Angew Chem Int Ed 45:7427–7430

    Article  CAS  Google Scholar 

  57. Amijs CHM, Ferrer C, Echavarren AM (2007) Chem Commun 698–700

  58. Amijs CHM, López-Carrillo V, Raducan M, Pérez-Galán P, Ferrer C, Echavarren AM (2008) J Org Chem 73:7721–7730

    Article  CAS  Google Scholar 

  59. Schlwies M, Dempwolff AL, Rominger F, Helmchen G (2007) Angew Chem Int Ed 46:5598–5601

    Article  CAS  Google Scholar 

  60. Schelwies M, Moser R, Dempwolff AL, Rominger F, Helmchen G (2009) Chem Eur J 15:10888–10900

    Article  CAS  Google Scholar 

  61. Fürstner A, Morency L (2008) Angew Chem Int Ed 47:5030–5033

    Article  CAS  Google Scholar 

  62. Seidel G, Mynott R, Fürstner A (2009) Angew Chem Int Ed 48:2510–2513

    Article  CAS  Google Scholar 

  63. Benitez D, Shapiro ND, Tkatchouk E, Wang Y, Goddard WA III, Toste DF (2009) Nat Chem 1:482–486

    Article  CAS  Google Scholar 

  64. Fedorov A, Moret M-E, Chen P (2008) J Am Chem Soc 130:8880–8881

    Article  CAS  Google Scholar 

  65. Fedorov A, Chen P (2009) Organometallics 28:1278–1281

    Article  CAS  Google Scholar 

  66. Leseurre L, Chao C-M, Seki T, Genin E, Toullec PY, Genêt J-P, Michelet V (2009) Tetrahedron 65:1911–1918

    Article  CAS  Google Scholar 

  67. Baskar B, Bae HJ, An SE, Cheong JY, Rhee YH, Duschek A, Kirsch SF (2008) Org Lett 10:2605–2607

    Article  CAS  Google Scholar 

  68. Chatani N, Kataoka K, Murai S, Furukawa N, Seki Y (1998) J Am Chem Soc 120:9104–9105

    Article  CAS  Google Scholar 

  69. Mainetti E, Mouriès V, Fensterbank L, Malacria M, Marco-Contelles J (2002) Angew Chem Int Ed 41:2132–2135

    Article  CAS  Google Scholar 

  70. Nieto-Oberhuber C, López S, Muñoz MP, Jiménez-Núñez E, Buñuel E, Cárdenas DJ, Echavarren AM (2006) Chem Eur J 12:1694–1702

    Article  CAS  Google Scholar 

  71. Jiménez-Núñez E, Claverie CK, Bour C, Cárdenas DJ, Echavarren AM (2008) Angew Chem Int Ed 47:7892–7895

    Article  CAS  Google Scholar 

  72. Jiménez-Núñez E, Claverie CK, Nieto-Oberhuber C, Echavarren AM (2006) Angew Chem Int Ed 45:5451–5455

    Article  CAS  Google Scholar 

  73. Jiménez-Núñez E, Raducan M, Lauterbach T, Molawi K, Solorio CR, Echavarren AM, Angew AM (2009) Chem. Int. Ed. 48:6152–6155

    Article  CAS  Google Scholar 

  74. Caine DS, Gupton JT (1975) J Org Chem 40:809–810

    Article  CAS  Google Scholar 

  75. Ishiyama H, Kozawa S, Aoyama K, Mikami Y, Fromont J, Kobayashi J (2008) J Nat Prod 71:1301–1303

    Article  CAS  Google Scholar 

  76. Cronan JM, Daviau TR, Pannell LK, Cardellina JH (1995) J Org Chem 60:6864–6865

    Article  CAS  Google Scholar 

  77. Brochinia CB, Roque NF (2000) J Braz Chem Soc 11:361–364

    Google Scholar 

  78. Yang Z, Chen H, Li Y (2003) Helv Chim Acta 86:3305–3309

    Article  CAS  Google Scholar 

  79. Kim SM, Park JH, Choi SY, Chung YK (2007) Angew Chem Int Ed 46:6172–6175

    Article  CAS  Google Scholar 

  80. Johansson MJ, Gorin DJ, Staben ST, Toste FD (2005) J Am Chem Soc 127:18002–18003

    Article  CAS  Google Scholar 

  81. Ma W-H, Huang H, Zhou P, Chen D-F (2009) J Nat Prod 72:676–678

    Article  CAS  Google Scholar 

  82. Urones JG, Sánchez I, Martín N, de Pascual-Teresa J, San Feliciano A (1989) Phytochemistry 28:183–187

    Article  CAS  Google Scholar 

  83. Escribano-Cuesta A, López-Carrillo V, Janssen D, Echavarren AM (2009) Chem Eur J 15:5646–5650

    Article  CAS  Google Scholar 

  84. Kusama H, Yamabe H, Onizawa Y, Hoshino T, Iwasawa N (2005) Angew Chem Int Ed 44:468–470

    Article  CAS  Google Scholar 

  85. Funami H, Kusama H, Iwasawa N (2007) Angew Chem Int Ed 46:909–911

    Article  CAS  Google Scholar 

  86. Oh CH, Lee JH, Lee SJ, Kim JI, Hong CS (2008) Angew Chem Int Ed 47:7505–7507

    Article  CAS  Google Scholar 

  87. Oh CH, Lee JH, Lee SM, Yi HJ, Hong CS (2009) Chem Eur J 15:71–74

    Article  CAS  Google Scholar 

  88. Bhunia S, Liu R-S (2008) J Am Chem Soc 130:16488–16489

    Article  CAS  Google Scholar 

  89. Lemière G, Gandon V, Cariou K, Hours A, Fukuyama T, Dhimane A-L, Fensterbank L, Malacria M (2009) J Am Chem Soc 131:2993–3006

    Article  CAS  Google Scholar 

  90. Horino Y, Yamamoto T, Ueda K, Kuroda S, Toste FD (2009) J Am Chem Soc 131:2809–2811

    Article  CAS  Google Scholar 

  91. Porcel S, López-Carrillo V, García-Yebra C, Echavarren AM (2008) Angew Chem Int Ed 47:1883–1886

    Article  CAS  Google Scholar 

  92. Jiménez-Núñez E, Molawi K, Echavarren AM (2009) Chem Commun 7327–7329

  93. Peng G-P, Tian G, Huang X-F, Lou F-C (2003) Phytochemistry 63:877–881

    Article  CAS  Google Scholar 

  94. Ratnayake R, Covell D, Ransom TT, Gustafson KR, Beutler JA (2009) Org Lett 11:57–60

    Article  CAS  Google Scholar 

  95. Willot M, Radtke L, Könning D, Fröhlich R, Gessner VH, Strohmann C, Christmann M (2009) Angew Chem Int Ed 48:9105–9108

    Article  CAS  Google Scholar 

  96. Umbreit MA, Sharpless KB (1981) Org Synth 60:29–32

    CAS  Google Scholar 

  97. Huang S-X, Yang J, Xiao W-L, Zhu Y-L, Li R-T, Li L-M, Pu J-X, Li X, Li S-H, Sun H-D (2006) Helv Chim Acta 89:1169–1175

    Article  CAS  Google Scholar 

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Acknowledgments

We thank the MICINN (CTQ2007-60745/BQU and Consolider Ingenio 2010, Grant CSD2006-0003, and FPU fellowship to E. J.-N.), the AGAUR (2009 SGR 47), and the ICIQ Foundation for financial support.

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  1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007, Tarragona, Spain

    Antonio M. Echavarren & Eloísa Jiménez-Núñez

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  1. Antonio M. Echavarren
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Correspondence to Antonio M. Echavarren.

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Echavarren, A.M., Jiménez-Núñez, E. Complexity via Gold-Catalyzed Molecular Gymnastics. Top Catal 53, 924–930 (2010). https://doi.org/10.1007/s11244-010-9524-6

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