Science China Chemistry

, Volume 59, Issue 9, pp 1065–1078 | Cite as

Asymmetric construction of all-carbon quaternary stereocenters in the total synthesis of natural products

Mini Reviews

Abstract

Structure units containing all-carbon quaternary stereogenic center are found in many bioactive natural products. However, enantioselective construction of this type of structure units has been a formidable challenge for synthetic community due to the steric hindrance enforced by all-carbon quaternary stereocenters. In this review, we present the achievements made by Chinese scientists in the area of asymmetric synthesis of all-carbon quaternary stereocenters in natural products during the past two years.

Keywords

all-carbon quaternary stereocenter asymmetric synthesis total synthesis natural product 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Schun Y, Cordell GA. J Nat Prod, 1985, 48: 969–971CrossRefGoogle Scholar
  2. 2.
    Zhou X, Xiao T, Iwama Y, Qin Y. Angew Chem Int Ed, 2012, 51: 4909–4912CrossRefGoogle Scholar
  3. 3.
    Chen X, Duan S, Tao C, Zhai H, Qiu FG. Nat Commun, 2016, 6: 7204–CrossRefGoogle Scholar
  4. 4.
    Moncrief JW, Lipscomb WN. Acta Cryst, 1966, 21: 322–331CrossRefGoogle Scholar
  5. 5.
    Ishikawa H, Colby DA, Seto S, Va P, Tam A, Kakei H, Rayl TJ, Hwang I, Boger DL. J Am Chem Soc, 2009, 131: 4904–4916CrossRefGoogle Scholar
  6. 6.
    Blakemore PR, White JD. Chem Commun, 2002, 1159–1168Google Scholar
  7. 7.
    Li Q, Zhang H. Chem Eur J, 2015, 21: 16379–16382CrossRefGoogle Scholar
  8. 8.
    Douglas CJ, Overman LE. Proc Natl Acad Sci, 2004, 101: 5363–5367CrossRefGoogle Scholar
  9. 9.
    Trost BM, Jiang C. Synthesis, 2006, 369–396Google Scholar
  10. 10.
    Das JP, Marek I. Chem Commun, 2011, 47: 4593–4623CrossRefGoogle Scholar
  11. 11.
    Repka LM, Reisman SE. J Org Chem, 2013, 78: 12314–12320CrossRefGoogle Scholar
  12. 12.
    Quasdorf KW, Overman LE. Nature, 2014, 516: 181–191CrossRefGoogle Scholar
  13. 13.
    Liu Y, Han SJ, Liu WB, Stoltz BM. Acc Chem Res, 2015, 48: 740–751CrossRefGoogle Scholar
  14. 14.
    Long R, Huang J, Gong J, Yang Z. Nat Prod Rep, 2015, 32: 1584–1601CrossRefGoogle Scholar
  15. 15.
    Büschleb M, Dorich S, Hanessian S, Tao D, Schenthal KB, Overman LE. Angew Chem Int Ed, 2016, 55: 4156–4186CrossRefGoogle Scholar
  16. 16.
    Zhou S, Jia Y. Org Lett, 2014, 16: 3416–3418CrossRefGoogle Scholar
  17. 17.
    Wang L, Wang H, Li Y, Tang P. Angew Chem Int Ed, 2015, 54: 5732–5735CrossRefGoogle Scholar
  18. 18.
    Wang X, Xia D, Tan L, Chen H, Huang H, Song H, Qin Y. Chem Eur J, 2015, 21: 14602–14607CrossRefGoogle Scholar
  19. 19.
    Shen Y, Li L, Pan Z, Wang Y, Li J, Wang K, Wang X, Zhang Y, Hu T, Zhang Y. Org Lett, 2015, 17: 5480–5483CrossRefGoogle Scholar
  20. 20.
    Jiang SZ, Lei T, Wei K, Yang YR. Org Lett, 2014, 16: 5612–5615CrossRefGoogle Scholar
  21. 21.
    Hong B, Li H, Wu J, Zhang J, Lei X. Angew Chem Int Ed, 2015, 54: 1011–1015CrossRefGoogle Scholar
  22. 22.
    Qin WF, Xiao T, Zhang D, Deng LF, Wang Y, Qin Y. Chem Commun, 2015, 51: 16143–16146CrossRefGoogle Scholar
  23. 23.
    Hong B, Li C, Wang Z, Chen J, Li H, Lei X. J Am Chem Soc, 2015, 137: 11946–11949CrossRefGoogle Scholar
  24. 24.
    Yin JP, Gu M, Li Y, Nan FJ. J Org Chem, 2014, 79: 6294–6301CrossRefGoogle Scholar
  25. 25.
    Du B, Yuan C, Yu T, Yang L, Yang Y, Liu B, Qin S. Chem Eur J, 2014, 20: 2613–2622CrossRefGoogle Scholar
  26. 26.
    Ren XD, Zhao N, Xu S, Lü HN, Ma SG, Liu YB, Li Y, Qu J, Yu SS. Tetrahedron, 2015, 71: 4821–4829CrossRefGoogle Scholar
  27. 27.
    Huang J, Fang L, Gong J, Li C, Yang Z. Tetrahedron, 2015, 71: 3720–3733CrossRefGoogle Scholar
  28. 28.
    You L, Liang XT, Xu LM, Wang YF, Zhang JJ, Su Q, Li YH, Zhang B, Yang SL, Chen JH, Yang Z. J Am Chem Soc, 2015, 137: 10120–10123CrossRefGoogle Scholar
  29. 29.
    Jin S, Gong J, Qin Y. Angew Chem Int Ed, 2015, 54: 2228–2231CrossRefGoogle Scholar
  30. 30.
    Huang HX, Jin SJ, Gong J, Zhang D, Song H, Qin Y. Chem Eur J, 2015, 21: 13284–13290CrossRefGoogle Scholar
  31. 31.
    Cabral G, Marques A, Schubert V, Pedrosa-Harand A, Schlögelhofer P. Nat Commun, 2014, 5: 5070–CrossRefGoogle Scholar
  32. 32.
    Sun Y, Chen P, Zhang D, Baunach M, Hertweck C, Li A. Angew Chem Int Ed, 2014, 53: 9012–9016CrossRefGoogle Scholar
  33. 33.
    Gao HT, Wang BL, Li WDZ. Tetrahedron, 2014, 70: 9436–9448CrossRefGoogle Scholar
  34. 34.
    Wang BL, Gao HT, Li WDZ. J Org Chem, 2015, 80: 5296–5301CrossRefGoogle Scholar
  35. 35.
    Xu S, Gu J, Li H, Ma D, Xie X, She X. Org Lett, 2014, 16: 1996–1999CrossRefGoogle Scholar
  36. 36.
    Xu H, Tang H, Feng H, Li Y. J Org Chem, 2014, 79: 10110–10122CrossRefGoogle Scholar
  37. 37.
    Zhao JC, Yu SM, Qiu HB, Yao ZJ. Tetrahedron, 2014, 70: 3197–3210CrossRefGoogle Scholar
  38. 38.
    Ren J, Liu Y, Song L, Tong R. Org Lett, 2014, 16: 2986–2989CrossRefGoogle Scholar
  39. 39.
    Shen X, Zhou Y, Xi Y, Zhao J, Zhang H. Chem Commun, 2015, 51: 14873–14876CrossRefGoogle Scholar
  40. 40.
    Wu X, Huang J, Guo B, Zhao L, Liu Y, Chen J, Cao W. Adv Synth Catal, 2014, 356: 3377–3382CrossRefGoogle Scholar
  41. 41.
    Tang Y, Liu J, Chen P, Lv M, Wang Z, Huang Y. J Org Chem, 2014, 79: 11729–11734CrossRefGoogle Scholar
  42. 42.
    Li L, Yang Q, Wang Y, Jia Y. Angew Chem Int Ed, 2015, 54: 6255–6259CrossRefGoogle Scholar
  43. 43.
    Du JY, Zeng C, Han XJ, Qu H, Zhao XH, An XT, Fan CA. J Am Chem Soc, 2015, 137: 4267–4273CrossRefGoogle Scholar
  44. 44.
    Deng J, Zhou S, Zhang W, Li J, Li R, Li A. J Am Chem Soc, 2014, 136: 8185–8188CrossRefGoogle Scholar
  45. 45.
    Zhou S, Chen H, Luo Y, Zhang W, Li A. Angew Chem Int Ed, 2015, 54: 6878–6882CrossRefGoogle Scholar
  46. 46.
    Huang JZ, Zhang CL, Zhu YF, Li LL, Chen DF, Han ZY, Gong LZ. Chem Eur J, 2015, 21: 8389–8393CrossRefGoogle Scholar
  47. 47.
    Li LQ, Li MM, Chen D, Liu HM, Geng H, Lin J, Qin HB. Tetrahedron Lett, 2014, 55: 5960–5962CrossRefGoogle Scholar
  48. 48.
    Shen XL, Zhao RR, Mo MJ, Peng FZ, Zhang HB, Shao ZH. J Org Chem, 2014, 79: 2473–2480CrossRefGoogle Scholar
  49. 49.
    Kuang L, Liu LL, Chiu P. Chem Eur J, 2015, 21: 14287–14291CrossRefGoogle Scholar
  50. 50.
    He C, Zhu C, Wang B, Ding H. Chem Eur J, 2014, 20: 15053–15060CrossRefGoogle Scholar
  51. 51.
    Meng Z, Yu H, Li L, Tao W, Chen H, Wan M, Yang P, Edmonds DJ, Zhong J, Li A. Nat Commun, 2015, 6: 6096–CrossRefGoogle Scholar
  52. 52.
    Marsden SP, Depew KM, Danishefsky SJ. J Am Chem Soc, 1994, 116: 11143–11144CrossRefGoogle Scholar
  53. 53.
    Lebrasseur N, Gagnepain J, Ozanne-Beaudenon A, Léger JM, Quideau S. J Org Chem, 2007, 72: 6280–6283CrossRefGoogle Scholar
  54. 54.
    Khand IU, Knox GR, Pauson PL, Watts WE, Foreman MI. J Chem Soc Perkin Trans 1, 1973, 977–981Google Scholar
  55. 55.
    Simmons HE, Smith RD. J Am Chem Soc, 1958, 80: 5323–5324CrossRefGoogle Scholar
  56. 56.
    Barton DHR, O’Brien RE, Sternhell S. J Chem Soc, 1962, 470–476Google Scholar
  57. 57.
    Bamford WR, Stevens TS. J Chem Soc, 1952, 4735–4740Google Scholar
  58. 58.
    Yoder RA, Johnston JN. Chem Rev, 2005, 105: 4730–4756CrossRefGoogle Scholar
  59. 59.
    Silva, LF, Olofsson B. Nat Prod Rep, 2011, 28: 1722–1754CrossRefGoogle Scholar
  60. 60.
    Liang J, Chen J, Du F, Zeng X, Li L, Zhang H. Org Lett, 2009, 11: 2820–2823CrossRefGoogle Scholar
  61. 61.
    Liang J, Chen J, Liu J, Li L, Zhang H. Chem Commun, 2010, 46: 3666–3668CrossRefGoogle Scholar
  62. 62.
    Xu Z, Huang K, Liu T, Xie M, Zhang H. Chem Commun, 2011, 47: 4923–4925CrossRefGoogle Scholar
  63. 63.
    Kiyotsuka Y, Acharya HP, Katayama Y, Hyodo T, Kobayashi Y. Org Lett, 2008, 10: 1719–1722CrossRefGoogle Scholar
  64. 64.
    Liu G, Cogan DA, Ellman JA. J Am Chem Soc, 1997, 119: 9913–9914CrossRefGoogle Scholar
  65. 65.
    Robak MAT, Herbage MA, Ellman JA. Chem Rev, 2010, 110: 3600–3740CrossRefGoogle Scholar
  66. 66.
    Zhou Y, Xi Y, Zhao J, Sheng X, Zhang S, Zhang H. Org Lett, 2012, 14: 3116–3119CrossRefGoogle Scholar
  67. 67.
    Chen W, Ren J, Wang M, Dang L, Shen X, Yang X, Zhang H. Chem Commun, 2014, 50: 6259–6262CrossRefGoogle Scholar
  68. 68.
    Tsogoeva SB. Eur J Org Chem, 2007, 2007: 1701–1716CrossRefGoogle Scholar
  69. 69.
    Jones SB, Simmons B, Mastracchio A, MacMillan DWC. Nature, 2011, 475: 183–188CrossRefGoogle Scholar
  70. 70.
    Liu XH, Lin LL, Feng XM. Acc Chem Res, 2011, 44: 574–587CrossRefGoogle Scholar
  71. 71.
    Hajos ZG, Parrish DR. J Org Chem, 1974, 39: 1615–1621CrossRefGoogle Scholar
  72. 72.
    Schafroth MA, Sarlah D, Krautwald S, Carreira EM. J Am Chem Soc, 2012, 134: 20276–20278CrossRefGoogle Scholar
  73. 73.
    Huang JZ, Wu X, Gong LZ. Adv Synth Catal, 2013, 355: 2531–2537CrossRefGoogle Scholar
  74. 74.
    Lin S, Lu X. Org Lett, 2010, 12: 2536–2539CrossRefGoogle Scholar
  75. 75.
    Kikushima K, Holder JC, Gatti M, Stoltz BM. J Am Chem Soc, 2011, 133: 6902–6905CrossRefGoogle Scholar
  76. 76.
    Tang S, Xu Y, He J, He Y, Zheng J, Pan X, She X. Org Lett, 2008, 10: 1855–1858CrossRefGoogle Scholar
  77. 77.
    Node M, Ozeki M, Planas L, Nakano M, Takita H, Mori D, Tamatani S, Kajimoto T. J Org Chem, 2010, 75: 190–196CrossRefGoogle Scholar
  78. 78.
    Li Z, Zhang S, Wu S, Shen X, Zou L, Wang F, Li X, Peng F, Zhang H, Shao Z. Angew Chem Int Ed, 2013, 52: 4117–4121CrossRefGoogle Scholar
  79. 79.
    Gartshore CJ, Lupton DW. Angew Chem Int Ed, 2013, 52: 4113–4116CrossRefGoogle Scholar
  80. 80.
    Fujii A, Hashiguchi S, Uematsu N, Ikariya T, Noyori R. J Am Chem Soc, 1996, 118: 2521–2522CrossRefGoogle Scholar
  81. 81.
    Touge T, Hakamata T, Nara H, Kobayashi T, Sayo N, Saito T, Kayaki Y, Ikariya T. J Am Chem Soc, 2011, 133: 14960–14963CrossRefGoogle Scholar
  82. 82.
    Nicolaou KC, Sun YP, Peng XS, Polet D, Chen DYK. Angew Chem Int Ed, 2008, 47: 7310–7313CrossRefGoogle Scholar
  83. 83.
    Nicolaou KC, Peng XS, Sun YP, Polet D, Zou B, Lim CS, Chen DYK. J Am Chem Soc, 2009, 131: 10587–10597CrossRefGoogle Scholar
  84. 84.
    Trost BM, Rise F. J Am Chem Soc, 1987, 109: 3161–3163CrossRefGoogle Scholar
  85. 85.
    Goeke A, Kuwano R, Ito Y, Sawamura M. Angew Chem Int Ed, 1996, 35: 662–663CrossRefGoogle Scholar
  86. 86.
    Hatano M, Terada M, Mikami K. Angew Chem Int Ed, 2001, 40: 249–253CrossRefGoogle Scholar

Copyright information

© Science China Press and Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  1. 1.Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and TechnologyYunnan UniversityKunmingChina

Personalised recommendations