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Gold Catalysis in the Synthesis of Natural Products: Heterocycle Construction via Direct C–X-Bond-Forming Reactions

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Au-Catalyzed Synthesis and Functionalization of Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 46))

Abstract

In this chapter, a summarization of the application of gold-catalyzed heterocycle synthesis involving direct C-X bond formation in natural product synthesis is given, with particular emphasis on the advantage of gold catalysis in tackling the chemo- and regioselectivity problem.

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References

  1. Gorin DJ, Toste FD (2007) Nature 446:395–403

    Article  CAS  Google Scholar 

  2. Leyva-Pérez A, Corma A (2012) Angew Chem Int Ed 51:614–635

    Article  CAS  Google Scholar 

  3. Hashmi ASK (2007) Chem Rev 107:3180–3211

    Article  CAS  Google Scholar 

  4. Li Z, Brouwer C, He C (2008) Chem Rev 108:3239–3265

    Article  CAS  Google Scholar 

  5. Arcadi A (2008) Chem Rev 108:3266–3325

    Article  CAS  Google Scholar 

  6. Corma A, Leyva-Pérez A, Sabater MJ (2011) Chem Rev 111:1657–1712

    Article  CAS  Google Scholar 

  7. Hashmi ASK, Rudolph M (2011) Chem Commun 47:6536–6544

    Article  CAS  Google Scholar 

  8. Fürstner A, Davies PW (2007) Angew Chem Int Ed 46:3410–3449

    Article  CAS  Google Scholar 

  9. Brenzovich WE (2012) Angew Chem Int Ed 51:8933–8935

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. Skouta R, Li CJ (2008) Tetrahedron 64:4917–4938

    Article  CAS  Google Scholar 

  12. Jiménez-Núñez E, Echavarren AM (2007) Chem Commun 333–346

    Google Scholar 

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

    Article  CAS  Google Scholar 

  14. Hashmi ASK, Frost TM, Bats JW (2000) J Am Chem Soc 122:11553–11554

    Article  CAS  Google Scholar 

  15. Hashmi ASK, Schwarz L, Choi JH, Frost TM (2000) Angew Chem Int Ed 39:2285–2288

    Article  CAS  Google Scholar 

  16. Kennedy-Smith JJ, Staben ST, Toste FD (2004) J Am Chem Soc 126:4526–4527

    Article  CAS  Google Scholar 

  17. Sherry BD, Toste FD (2004) J Am Chem Soc 126:15978–15979

    Article  CAS  Google Scholar 

  18. 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 

  19. Zhang L, Kozmin SA (2004) J Am Chem Soc 126:11806–11807

    Article  CAS  Google Scholar 

  20. Hashmi ASK, Rudolph M (2008) Chem Soc Rev 37:1766–1775

    Article  CAS  Google Scholar 

  21. Rudolph M, Hashmi ASK (2012) Chem Soc Rev 41:2448–2462

    Article  CAS  Google Scholar 

  22. Zhang Y, Luo T, Yang Z (2014) Nat Prod Rep 31:489–503

    Article  CAS  Google Scholar 

  23. Zeldin RM, Toste FD (2011) Chem Sci 2:1706–1709

    Article  CAS  Google Scholar 

  24. Teller H, Fürstner A (2011) Chem Eur J 17:7764–7767

    Article  CAS  Google Scholar 

  25. Lu Z, Li Y, Deng J, Li A (2013) Nat Chem 5:679–684

    Article  CAS  Google Scholar 

  26. González AZ, Benitez D, Tkatchouk E, Goddard WA III, Toste FD (2011) J Am Chem Soc 133:5500–5507

    Article  CAS  Google Scholar 

  27. Liu Z, Wasmuth AS, Nelson SG (2006) J Am Chem Soc 128:10352–10353

    Article  CAS  Google Scholar 

  28. Cui L, Peng Y, Zhang L (2009) J Am Chem Soc 131:8394–8395

    Article  CAS  Google Scholar 

  29. Zhang L, Cui L (2010) Sci China: Chem 53:113–118

    Google Scholar 

  30. Shan ZH, Liu J, Xu LM, Tang YF, Chen JH, Yang Z (2012) Org Lett 14:3712–3715

    Article  CAS  Google Scholar 

  31. Trost BM, Dong G (2008) Nature 456:485–488

    Article  CAS  Google Scholar 

  32. Trost BM, Dong G (2010) J Am Chem Soc 132:16403–16416

    Article  CAS  Google Scholar 

  33. Pettit GR, Gao F, Blumberg PM, Herald CL, Coll JC, Kamano Y, Lewin NE, Schmidt JM, Chapuis JC (1996) J Nat Prod 59:286–289

    Article  CAS  Google Scholar 

  34. Trost BM, Yang H, Thiel OR, Frontier AJ, Brindle CS (2007) J Am Chem Soc 129:2206–2207

    Article  CAS  Google Scholar 

  35. Bihelovic F, Saicic RN (2012) Angew Chem Int Ed 51:5687–5691

    Article  CAS  Google Scholar 

  36. Bihelovic F, Karadzic I, Matovic R, Saicic RN (2013) Org Biomol Chem 11:5413–5424

    Article  CAS  Google Scholar 

  37. Bister B, Bischoff D, Ströbele M, Riedlinger J, Reicke A, Wolter F, Bull AT, Zähner H, Fiedler HP, Süssmuth RD (2004) Angew Chem Int Ed 43:2574–2576

    Article  CAS  Google Scholar 

  38. Benson S, Collin MP, Arlt A, Gabor B, Goddard R, Fürstner A (2011) Angew Chem Int Ed 50:8739–8744

    Article  CAS  Google Scholar 

  39. Pettit GR, Inoue M, Kamano Y, Herald DL, Arm C, Dufresne C, Christie ND, Schmidt JM, Doubek DL, Krupa TS (1988) J Am Chem Soc 110:2006–2007

    Article  CAS  Google Scholar 

  40. Serrano M (1997) Exp Cell Res 237:7–13

    Article  CAS  Google Scholar 

  41. Fortner KC, Kato D, Tanaka Y, Shair MD (2010) J Am Chem Soc 132:275–280

    Article  CAS  Google Scholar 

  42. Fernández A, Levine ZG, Baumann M, Sulzer-Mossé S, Sparr C, Schläger S, Metzger A, Baxendale IR, Ley SV (2013) Synlett 24:514–518

    Article  CAS  Google Scholar 

  43. Higa T, Tanaka J, Kitamura A, Koyama T, Takahashi M, Uchida T (1994) Pure Appl Chem 66:2227–2230

    Article  CAS  Google Scholar 

  44. Christen AA, Peaden RN (1981) Plant Dis 65:319–321

    Article  Google Scholar 

  45. Lin Y, Wu X, Feng S, Jiang G, Luo J, Zhou S, Vrijmoed LLP, Jones EBG, Krohn K, Steingrover K, Zsila F (2001) J Org Chem 66:6252–6256

    Article  CAS  Google Scholar 

  46. Panda B, Sarkar TK (2013) J Org Chem 78:2413–2421

    Article  CAS  Google Scholar 

  47. Sarkar D, Venkateswaran RV (2011) Tetrahedron 67:4559–4568

    Article  CAS  Google Scholar 

  48. Feng Y, Jiang X, De Brabander JK (2012) J Am Chem Soc 134:17083–17093

    Article  CAS  Google Scholar 

  49. Trost BM, O’Boyle BM, Hund D (2009) J Am Chem Soc 131:15061–15074

    Article  CAS  Google Scholar 

  50. Takahashi K, Yoshihara T, Kurosawa K (2005) J Antibiot 58:420–424

    Article  CAS  Google Scholar 

  51. Tachibana K, Scheuer PJ, Tsukitani Y, Kikuchi H, Van Engen D, Clardy J, Gopichand Y, Schimtz FJ (1981) J Am Chem Soc 103:2469–2471

    Article  CAS  Google Scholar 

  52. Fang C, Pang Y, Forsyth CJ (2010) Org Lett 12:4528–4531

    Article  CAS  Google Scholar 

  53. Isobe M, Ichikawa Y, Goto T (1986) Tetrahedron Lett 27:963–966

    Article  CAS  Google Scholar 

  54. Isobe M, Ichikawa Y, Bai DL, Masaki H, Goto T (1987) Tetrahedron 43:4767–4776

    Article  CAS  Google Scholar 

  55. Ley SV, Humphries AC, Eick H, Downham R, Ross AR, Boyce RJ, Pavey JBJ, Pietruszka J (1998) J Chem Soc Perkin Trans 1 (23):3907–3911

    Google Scholar 

  56. Kona CN, Ramana CV (2014) Tetrahedron 70:3653–3656

    Article  CAS  Google Scholar 

  57. Tlais SF, Dudley GB (2010) Org Lett 12:4698–4701

    Article  CAS  Google Scholar 

  58. Tlais SF, Dudley GB (2011) Beilstein J Org Chem 7:570–577

    Article  CAS  Google Scholar 

  59. Li X, Yao Y, Zheng Y, Sattler I, Lin W (2007) Arch Phram Res 30:812–815

    Article  CAS  Google Scholar 

  60. Li Y, Zhou F, Forsyth CJ (2007) Angew Chem Int Ed 46:279–282

    Article  CAS  Google Scholar 

  61. Hoffmeister L, Fukuda T, Pototschnig G, Fürstner A (2015) Chem Eur J 21:4529–4533

    Article  CAS  Google Scholar 

  62. Kazlauskas R, Murphy PT, Wells RJ, Blackman AJ (1982) Aust J Chem 35:113–120

    Article  CAS  Google Scholar 

  63. Chaładaj W, Corbet M, Fürstner A (2012) Angew Chem Int Ed 51:6929–6933

    Article  CAS  Google Scholar 

  64. Stout EP, Hasemeyer AP, Lane AL, Davenport TM, Engel S, Hay ME, Fairchild CR, Prudhomme J, Le Roch K, Aalbersberg W, Kubanek J (2009) Org Lett 11:225–228

    Article  CAS  Google Scholar 

  65. Lee JS, Shin J, Shin HJ, Lee HS, Lee YJ, Lee HS, Won H (2014) Eur J Org Chem 2014:4472–4476

    Google Scholar 

  66. Chen Y, Wang L, Sun N, Xie X, Zhou X, Chen H, Li Y, Liu Y (2014) Chem Eur J 20:12015–12019

    Article  CAS  Google Scholar 

  67. Wang C, Chen Y, Xie X, Liu J, Liu Y (2012) J Org Chem 77:1915–1921

    Article  CAS  Google Scholar 

  68. Kono K, Tanaka M, Ono Y, Hosoya T, Ogita T, Kohama T (2001) J Antibiot 4:415–420

    Article  Google Scholar 

  69. Zhu J, Germain AR, Porco JA Jr (2004) Angew Chem Int Ed 43:1239–1243

    Article  CAS  Google Scholar 

  70. Ma S (2005) Chem Rev 105:2829–2872

    Article  Google Scholar 

  71. Pan F, Fu C, Ma S (2004) Chin J Org Chem 24:1168–1190

    CAS  Google Scholar 

  72. Ma S (2003) Acc Chem Res 36:701–712

    Article  CAS  Google Scholar 

  73. Ma S (2009) Acc Chem Res 42:1679–1688

    Article  CAS  Google Scholar 

  74. Hashmi ASK (2000) Angew Chem Int Ed 39:3590–3593

    Article  CAS  Google Scholar 

  75. Hoffmann-Röder A, Krause N (2001) Org Lett 3:2537–2538

    Article  CAS  Google Scholar 

  76. Krause N, Hoffmann-Röder A, Canisius J (2002) Synthesis 1759–1774

    Google Scholar 

  77. Marshall JA, Pinney KG (1993) J Org Chem 58:7180–7184

    Article  CAS  Google Scholar 

  78. Naves YR, Bachmann P (1945) Helv Chim Acta 28:1227–1230

    Article  CAS  Google Scholar 

  79. Kawakami M, Ganguly SN, Banerjee J, Kobayashi A (1995) J Agric Food Chem 43:200–207

    Article  CAS  Google Scholar 

  80. Wüst M, Mosandl A (1999) Eur Food Res Technol 209:3–11

    Article  Google Scholar 

  81. Wang D, Ando K, Morita K, Kubota K, Kobayashi A (1994) Biosci Biotechnol Biochem 58:2050–2053

    Article  CAS  Google Scholar 

  82. Ito Y, Sugimoto A, Kakuda T, Kubota K (2002) J Agric Food Chem 50:4878–4884

    Article  CAS  Google Scholar 

  83. Bentley R (2006) Chem Rev 106:4099–4112

    Article  CAS  Google Scholar 

  84. Volz F, Wadman SH, Hoffmann-Röder A, Krause N (2009) Tetrahedron 65:1902–1910

    Article  CAS  Google Scholar 

  85. Volz F, Krause N (2007) Org Biomol Chem 5:1519–1521

    Article  CAS  Google Scholar 

  86. Phuong NM, Sung TV, Porzel A, Schmidt J, Merzweiler K, Adam G (1999) Phytochemistry 52:1725–1729

    Article  CAS  Google Scholar 

  87. Sawama Y, Sawama Y, Krause N (2008) Org Biomol Chem 6:3573–3579

    Article  CAS  Google Scholar 

  88. Jeker OF, Carreira EM (2012) Angew Chem Int Ed 51:3474–3477

    Article  CAS  Google Scholar 

  89. Okada T, Sakaguchi K, Shinada T, Ohfune Y (2011) Tetrahedron Lett 52:5744–5746

    Article  CAS  Google Scholar 

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

    Google Scholar 

  91. Zhou Q, Chen X, Ma D (2010) Angew Chem Int Ed 49:3513–3516

    Article  CAS  Google Scholar 

  92. Molawi K, Delpont N, Echavarren AM (2010) Angew Chem Int Ed 49:3517–3519

    Article  CAS  Google Scholar 

  93. Shi H, Fang L, Tan C, Shi L, Zhang W, Li CC, Luo T, Yang Z (2011) J Am Chem Soc 133:14944–14947

    Article  CAS  Google Scholar 

  94. Bernardeli P, Paquette LA (1998) Heterocycles 49:531–556

    Article  Google Scholar 

  95. Ellis JM, Crimmins MT (2008) Chem Rev 108:5278–5298

    Article  CAS  Google Scholar 

  96. Welford AJ, Collins I (2011) J Nat Prod 74:2318–2328

    Article  CAS  Google Scholar 

  97. Yue G, Zhang Y, Fang L, Li CC, Luo T, Yang Z (2014) Angew Chem Int Ed 53:1837–1840

    Article  CAS  Google Scholar 

  98. Unsworth WP, Stevens K, Lamont SG, Robertson J (2011) Chem Commun 47:7659–7661

    Article  CAS  Google Scholar 

  99. Colegate SM, Din LB, Latiff A, Salleh KM, Samsudin MW, Skelton BW, Tadano KI, White AH, Zakaria Z (1990) Phytochemistry 29:1701–1704

    Article  CAS  Google Scholar 

  100. Skouta R, Li CJ (2007) Angew Chem Int Ed 46:1117–1119

    Article  CAS  Google Scholar 

  101. Máximo P, Lourenço A (1998) Phytochemistry 48:359–362

    Article  Google Scholar 

  102. Holder CL, Churchwell MI, Doerge DR (1999) J Agric Food Chem 47:3764–3770

    Article  CAS  Google Scholar 

  103. Hendrich S, Lee KW, Xu X, Wang HJ, Murphy PA (1994) J Nutr 124:1789S–1792S

    CAS  Google Scholar 

  104. Skouta R, Li CJ (2007) Tetrahedron Lett 48:8343–8346

    Article  CAS  Google Scholar 

  105. Fukuda Y, Utimoto K, Nozaki H (1987) Heterocycles 25:297–300

    Article  CAS  Google Scholar 

  106. Fukuda Y, Utimoto K (1991) Synthesis 975–978

    Google Scholar 

  107. Gouault N, Le Roch M, de Pinto GC, David M (2012) Org Biomol Chem 10:5541–5546

    Article  CAS  Google Scholar 

  108. Trinh TTH, Nguyen KH, de Amaral PA, Gouault N (2013) Beilstein J Org Chem 9:2042–2047

    Article  CAS  Google Scholar 

  109. Chiba H, Oishi S, Fujii N, Ohno H (2012) Angew Chem Int Ed 51:9169–9172

    Article  CAS  Google Scholar 

  110. Chiba H, Sakai Y, Ohara A, Oishi S, Fujii N, Ohno H (2013) Chem Eur J 19:8875–8883

    Article  CAS  Google Scholar 

  111. Siengalewicz P, Rinner U, Mulzer J (2008) Chem Soc Rev 37:2676–2690

    Article  CAS  Google Scholar 

  112. Kahsai AW, Zhu S, Wardrop DJ, Lane WS, Fenteany G (2006) Chem Biol 13:973–983

    Article  CAS  Google Scholar 

  113. Taira Z, Matsumoto M, Ishida S, Icikawa T, Sakiya Y (1994) Chem Pharm Bull 42:1556–1561

    Article  CAS  Google Scholar 

  114. Enomoto T, Girard AL, Yasui Y, Takemoto Y (2009) J Org Chem 74:9158–9164

    Article  CAS  Google Scholar 

  115. Hanaoka M, Yamagishi H, Marutani M, Mukai C (1987) Chem Pharm Bull 35:2348–2354

    Article  CAS  Google Scholar 

  116. Sugimoto K, Toyoshima K, Nonaka S, Kotaki K, Ueda H, Tokuyama H (2013) Angew Chem Int Ed 52:7168–7171

    Article  CAS  Google Scholar 

  117. David B, Sévenet T, Morgat M, Guénard D, Moisand A, Tollon Y, Thoison O, Wright M (1994) Cell Motil Cytoskeleton 28:317–326

    Article  CAS  Google Scholar 

  118. Crawley SL, Funk RL (2006) Org Lett 8:3995–3998

    Article  CAS  Google Scholar 

  119. Nakajima R, Ogino T, Yokoshima S, Fukuyama T (2010) J Am Chem Soc 132:1236–1237

    Article  CAS  Google Scholar 

  120. Wang C, Sperry J (2011) Org Lett 13:6444–6447

    Article  CAS  Google Scholar 

  121. Gao Q, Garcia-Pichel F (2011) Nat Rev Microbiol 9:791–802

    Article  CAS  Google Scholar 

  122. Bates RW, Dewey MR (2009) Org Lett 11:3706–3708

    Article  CAS  Google Scholar 

  123. Oredipe OA, Furbert-Harris PM, Green WR, White SL, Olden K, Laniyan I, Parish-Gause D, Vaughn T, Griffin WM, Sridhar R (2003) Pharm Res 47:69–74

    Article  CAS  Google Scholar 

  124. Oredipe OA, Furbert-harris PM, Laniyan I, Green WR, Griffin WM, Sridhar R (2003) Cell Mol Biol 49:1089–1099

    CAS  Google Scholar 

  125. Buschmann N, Rückert A, Blechert S (2002) J Org Chem 67:4325–4329

    Article  CAS  Google Scholar 

  126. Mill S, Hootelé C (2000) J Nat Prod 63:762–764

    Article  CAS  Google Scholar 

  127. Jung HH, Floreancig PE (2007) J Org Chem 72:7359–7366

    Article  CAS  Google Scholar 

  128. Wu Y, Peng S, Ouyang Y, Qian P, He W, Xiang J (2012) Acta Chim Sin 70:1367–1370

    Article  CAS  Google Scholar 

  129. Gorin DJ, Davis NR, Toste FD (2005) J Am Chem Soc 127:11260–11261

    Article  CAS  Google Scholar 

  130. Hiroya K, Matsumoto S, Ashikawa M, Ogiwara K, Sakamoto T (2006) Org Lett 8:5349–5352

    Article  CAS  Google Scholar 

  131. Yan ZY, Xiao Y, Zhang L (2012) Angew Chem Int Ed 51:8624–8627

    Article  CAS  Google Scholar 

  132. Allen GR, Poletto JF, Weiss MJ (1965) J Org Chem 30:2897–2904

    Article  CAS  Google Scholar 

  133. Ito Y, Sawamura M, Hayashi T (1986) J Am Chem Soc 108:6405–6406

    Article  CAS  Google Scholar 

  134. Ito Y, Sawamura M, Hayashi T (1988) Tetrahedron Lett 29:239–240

    Article  CAS  Google Scholar 

  135. Hughes PF, Smith SH, Olson JT (1994) J Org Chem 59:5799–5802

    Article  CAS  Google Scholar 

  136. Kulanthaivel P, Hallock YF, Boros C, Hamilton SM, Janzen WP, Ballas LM, Loomis CR, Jiang JB, Katz B, Steiner JR, Clardy J (1993) J Am Chem Soc 115:6452–6453

    Article  CAS  Google Scholar 

  137. Bachi MD, Melman A (1997) J Org Chem 62:1896–1898

    Article  CAS  Google Scholar 

  138. Togni A, Pastor SD, Rihs G (1989) Helv Chim Acta 72:1471–1478

    Article  CAS  Google Scholar 

  139. Wenger RM (1985) Angew Chem Int Ed Engl 24:77–85

    Article  Google Scholar 

  140. Li J, Ji K, Zheng R, Nelson J, Zhang L (2014) Chem Commun 50:4130–4133

    Article  CAS  Google Scholar 

  141. Zhou J (2014) Multicatalyst system in asymmetric catalysis. Wiley, New York

    Book  Google Scholar 

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Wang, YH., Cao, ZY., Zhou, J. (2016). Gold Catalysis in the Synthesis of Natural Products: Heterocycle Construction via Direct C–X-Bond-Forming Reactions. In: Bandini, M. (eds) Au-Catalyzed Synthesis and Functionalization of Heterocycles. Topics in Heterocyclic Chemistry, vol 46. Springer, Cham. https://doi.org/10.1007/7081_2015_5007

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