Skip to main content
SpringerLink
Log in

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

  • Mini Reviews
  • Published:
Science China Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Schun Y, Cordell GA. J Nat Prod, 1985, 48: 969–971

    Article  CAS  Google Scholar 

  2. Zhou X, Xiao T, Iwama Y, Qin Y. Angew Chem Int Ed, 2012, 51: 4909–4912

    Article  CAS  Google Scholar 

  3. Chen X, Duan S, Tao C, Zhai H, Qiu FG. Nat Commun, 2016, 6: 7204–

    Article  Google Scholar 

  4. Moncrief JW, Lipscomb WN. Acta Cryst, 1966, 21: 322–331

    Article  CAS  Google Scholar 

  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: 4904–4916

    Article  CAS  Google Scholar 

  6. Blakemore PR, White JD. Chem Commun, 2002, 1159–1168

    Google Scholar 

  7. Li Q, Zhang H. Chem Eur J, 2015, 21: 16379–16382

    Article  CAS  Google Scholar 

  8. Douglas CJ, Overman LE. Proc Natl Acad Sci, 2004, 101: 5363–5367

    Article  CAS  Google Scholar 

  9. Trost BM, Jiang C. Synthesis, 2006, 369–396

    Google Scholar 

  10. Das JP, Marek I. Chem Commun, 2011, 47: 4593–4623

    Article  CAS  Google Scholar 

  11. Repka LM, Reisman SE. J Org Chem, 2013, 78: 12314–12320

    Article  CAS  Google Scholar 

  12. Quasdorf KW, Overman LE. Nature, 2014, 516: 181–191

    Article  CAS  Google Scholar 

  13. Liu Y, Han SJ, Liu WB, Stoltz BM. Acc Chem Res, 2015, 48: 740–751

    Article  CAS  Google Scholar 

  14. Long R, Huang J, Gong J, Yang Z. Nat Prod Rep, 2015, 32: 1584–1601

    Article  CAS  Google Scholar 

  15. Büschleb M, Dorich S, Hanessian S, Tao D, Schenthal KB, Overman LE. Angew Chem Int Ed, 2016, 55: 4156–4186

    Article  Google Scholar 

  16. Zhou S, Jia Y. Org Lett, 2014, 16: 3416–3418

    Article  CAS  Google Scholar 

  17. Wang L, Wang H, Li Y, Tang P. Angew Chem Int Ed, 2015, 54: 5732–5735

    Article  CAS  Google Scholar 

  18. Wang X, Xia D, Tan L, Chen H, Huang H, Song H, Qin Y. Chem Eur J, 2015, 21: 14602–14607

    Article  CAS  Google Scholar 

  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: 5480–5483

    Article  CAS  Google Scholar 

  20. Jiang SZ, Lei T, Wei K, Yang YR. Org Lett, 2014, 16: 5612–5615

    Article  CAS  Google Scholar 

  21. Hong B, Li H, Wu J, Zhang J, Lei X. Angew Chem Int Ed, 2015, 54: 1011–1015

    Article  CAS  Google Scholar 

  22. Qin WF, Xiao T, Zhang D, Deng LF, Wang Y, Qin Y. Chem Commun, 2015, 51: 16143–16146

    Article  CAS  Google Scholar 

  23. Hong B, Li C, Wang Z, Chen J, Li H, Lei X. J Am Chem Soc, 2015, 137: 11946–11949

    Article  CAS  Google Scholar 

  24. Yin JP, Gu M, Li Y, Nan FJ. J Org Chem, 2014, 79: 6294–6301

    Article  CAS  Google Scholar 

  25. Du B, Yuan C, Yu T, Yang L, Yang Y, Liu B, Qin S. Chem Eur J, 2014, 20: 2613–2622

    Article  CAS  Google Scholar 

  26. Ren XD, Zhao N, Xu S, Lü HN, Ma SG, Liu YB, Li Y, Qu J, Yu SS. Tetrahedron, 2015, 71: 4821–4829

    Article  CAS  Google Scholar 

  27. Huang J, Fang L, Gong J, Li C, Yang Z. Tetrahedron, 2015, 71: 3720–3733

    Article  CAS  Google Scholar 

  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: 10120–10123

    Article  CAS  Google Scholar 

  29. Jin S, Gong J, Qin Y. Angew Chem Int Ed, 2015, 54: 2228–2231

    Article  CAS  Google Scholar 

  30. Huang HX, Jin SJ, Gong J, Zhang D, Song H, Qin Y. Chem Eur J, 2015, 21: 13284–13290

    Article  CAS  Google Scholar 

  31. Cabral G, Marques A, Schubert V, Pedrosa-Harand A, Schlögelhofer P. Nat Commun, 2014, 5: 5070–

    Article  CAS  Google Scholar 

  32. Sun Y, Chen P, Zhang D, Baunach M, Hertweck C, Li A. Angew Chem Int Ed, 2014, 53: 9012–9016

    Article  CAS  Google Scholar 

  33. Gao HT, Wang BL, Li WDZ. Tetrahedron, 2014, 70: 9436–9448

    Article  CAS  Google Scholar 

  34. Wang BL, Gao HT, Li WDZ. J Org Chem, 2015, 80: 5296–5301

    Article  CAS  Google Scholar 

  35. Xu S, Gu J, Li H, Ma D, Xie X, She X. Org Lett, 2014, 16: 1996–1999

    Article  CAS  Google Scholar 

  36. Xu H, Tang H, Feng H, Li Y. J Org Chem, 2014, 79: 10110–10122

    Article  CAS  Google Scholar 

  37. Zhao JC, Yu SM, Qiu HB, Yao ZJ. Tetrahedron, 2014, 70: 3197–3210

    Article  CAS  Google Scholar 

  38. Ren J, Liu Y, Song L, Tong R. Org Lett, 2014, 16: 2986–2989

    Article  CAS  Google Scholar 

  39. Shen X, Zhou Y, Xi Y, Zhao J, Zhang H. Chem Commun, 2015, 51: 14873–14876

    Article  CAS  Google Scholar 

  40. Wu X, Huang J, Guo B, Zhao L, Liu Y, Chen J, Cao W. Adv Synth Catal, 2014, 356: 3377–3382

    Article  CAS  Google Scholar 

  41. Tang Y, Liu J, Chen P, Lv M, Wang Z, Huang Y. J Org Chem, 2014, 79: 11729–11734

    Article  CAS  Google Scholar 

  42. Li L, Yang Q, Wang Y, Jia Y. Angew Chem Int Ed, 2015, 54: 6255–6259

    Article  CAS  Google Scholar 

  43. Du JY, Zeng C, Han XJ, Qu H, Zhao XH, An XT, Fan CA. J Am Chem Soc, 2015, 137: 4267–4273

    Article  CAS  Google Scholar 

  44. Deng J, Zhou S, Zhang W, Li J, Li R, Li A. J Am Chem Soc, 2014, 136: 8185–8188

    Article  CAS  Google Scholar 

  45. Zhou S, Chen H, Luo Y, Zhang W, Li A. Angew Chem Int Ed, 2015, 54: 6878–6882

    Article  CAS  Google Scholar 

  46. Huang JZ, Zhang CL, Zhu YF, Li LL, Chen DF, Han ZY, Gong LZ. Chem Eur J, 2015, 21: 8389–8393

    Article  CAS  Google Scholar 

  47. Li LQ, Li MM, Chen D, Liu HM, Geng H, Lin J, Qin HB. Tetrahedron Lett, 2014, 55: 5960–5962

    Article  CAS  Google Scholar 

  48. Shen XL, Zhao RR, Mo MJ, Peng FZ, Zhang HB, Shao ZH. J Org Chem, 2014, 79: 2473–2480

    Article  CAS  Google Scholar 

  49. Kuang L, Liu LL, Chiu P. Chem Eur J, 2015, 21: 14287–14291

    Article  CAS  Google Scholar 

  50. He C, Zhu C, Wang B, Ding H. Chem Eur J, 2014, 20: 15053–15060

    Article  CAS  Google Scholar 

  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–

    Article  CAS  Google Scholar 

  52. Marsden SP, Depew KM, Danishefsky SJ. J Am Chem Soc, 1994, 116: 11143–11144

    Article  CAS  Google Scholar 

  53. Lebrasseur N, Gagnepain J, Ozanne-Beaudenon A, Léger JM, Quideau S. J Org Chem, 2007, 72: 6280–6283

    Article  CAS  Google Scholar 

  54. Khand IU, Knox GR, Pauson PL, Watts WE, Foreman MI. J Chem Soc Perkin Trans 1, 1973, 977–981

    Google Scholar 

  55. Simmons HE, Smith RD. J Am Chem Soc, 1958, 80: 5323–5324

    Article  CAS  Google Scholar 

  56. Barton DHR, O’Brien RE, Sternhell S. J Chem Soc, 1962, 470–476

    Google Scholar 

  57. Bamford WR, Stevens TS. J Chem Soc, 1952, 4735–4740

    Google Scholar 

  58. Yoder RA, Johnston JN. Chem Rev, 2005, 105: 4730–4756

    Article  CAS  Google Scholar 

  59. Silva, LF, Olofsson B. Nat Prod Rep, 2011, 28: 1722–1754

    Article  CAS  Google Scholar 

  60. Liang J, Chen J, Du F, Zeng X, Li L, Zhang H. Org Lett, 2009, 11: 2820–2823

    Article  CAS  Google Scholar 

  61. Liang J, Chen J, Liu J, Li L, Zhang H. Chem Commun, 2010, 46: 3666–3668

    Article  CAS  Google Scholar 

  62. Xu Z, Huang K, Liu T, Xie M, Zhang H. Chem Commun, 2011, 47: 4923–4925

    Article  CAS  Google Scholar 

  63. Kiyotsuka Y, Acharya HP, Katayama Y, Hyodo T, Kobayashi Y. Org Lett, 2008, 10: 1719–1722

    Article  CAS  Google Scholar 

  64. Liu G, Cogan DA, Ellman JA. J Am Chem Soc, 1997, 119: 9913–9914

    Article  CAS  Google Scholar 

  65. Robak MAT, Herbage MA, Ellman JA. Chem Rev, 2010, 110: 3600–3740

    Article  CAS  Google Scholar 

  66. Zhou Y, Xi Y, Zhao J, Sheng X, Zhang S, Zhang H. Org Lett, 2012, 14: 3116–3119

    Article  CAS  Google Scholar 

  67. Chen W, Ren J, Wang M, Dang L, Shen X, Yang X, Zhang H. Chem Commun, 2014, 50: 6259–6262

    Article  CAS  Google Scholar 

  68. Tsogoeva SB. Eur J Org Chem, 2007, 2007: 1701–1716

    Article  Google Scholar 

  69. Jones SB, Simmons B, Mastracchio A, MacMillan DWC. Nature, 2011, 475: 183–188

    Article  CAS  Google Scholar 

  70. Liu XH, Lin LL, Feng XM. Acc Chem Res, 2011, 44: 574–587

    Article  CAS  Google Scholar 

  71. Hajos ZG, Parrish DR. J Org Chem, 1974, 39: 1615–1621

    Article  CAS  Google Scholar 

  72. Schafroth MA, Sarlah D, Krautwald S, Carreira EM. J Am Chem Soc, 2012, 134: 20276–20278

    Article  CAS  Google Scholar 

  73. Huang JZ, Wu X, Gong LZ. Adv Synth Catal, 2013, 355: 2531–2537

    Article  CAS  Google Scholar 

  74. Lin S, Lu X. Org Lett, 2010, 12: 2536–2539

    Article  CAS  Google Scholar 

  75. Kikushima K, Holder JC, Gatti M, Stoltz BM. J Am Chem Soc, 2011, 133: 6902–6905

    Article  CAS  Google Scholar 

  76. Tang S, Xu Y, He J, He Y, Zheng J, Pan X, She X. Org Lett, 2008, 10: 1855–1858

    Article  CAS  Google Scholar 

  77. Node M, Ozeki M, Planas L, Nakano M, Takita H, Mori D, Tamatani S, Kajimoto T. J Org Chem, 2010, 75: 190–196

    Article  CAS  Google Scholar 

  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: 4117–4121

    Article  CAS  Google Scholar 

  79. Gartshore CJ, Lupton DW. Angew Chem Int Ed, 2013, 52: 4113–4116

    Article  CAS  Google Scholar 

  80. Fujii A, Hashiguchi S, Uematsu N, Ikariya T, Noyori R. J Am Chem Soc, 1996, 118: 2521–2522

    Article  CAS  Google Scholar 

  81. Touge T, Hakamata T, Nara H, Kobayashi T, Sayo N, Saito T, Kayaki Y, Ikariya T. J Am Chem Soc, 2011, 133: 14960–14963

    Article  CAS  Google Scholar 

  82. Nicolaou KC, Sun YP, Peng XS, Polet D, Chen DYK. Angew Chem Int Ed, 2008, 47: 7310–7313

    Article  CAS  Google Scholar 

  83. Nicolaou KC, Peng XS, Sun YP, Polet D, Zou B, Lim CS, Chen DYK. J Am Chem Soc, 2009, 131: 10587–10597

    Article  CAS  Google Scholar 

  84. Trost BM, Rise F. J Am Chem Soc, 1987, 109: 3161–3163

    Article  CAS  Google Scholar 

  85. Goeke A, Kuwano R, Ito Y, Sawamura M. Angew Chem Int Ed, 1996, 35: 662–663

    Article  CAS  Google Scholar 

  86. Hatano M, Terada M, Mikami K. Angew Chem Int Ed, 2001, 40: 249–253

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China

    Wen Chen & Hongbin Zhang

Authors
  1. Wen Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hongbin Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hongbin Zhang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chen, W., Zhang, H. Asymmetric construction of all-carbon quaternary stereocenters in the total synthesis of natural products. Sci. China Chem. 59, 1065–1078 (2016). https://doi.org/10.1007/s11426-016-0055-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-016-0055-0

Keywords

Search

Navigation