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Progress in Chemistry 2012, Vol. Issue (9): 1742-1750 Previous Articles   Next Articles

• Review •

Synthesis of Sesquiterpenoids: Englerin A and Its Analogues

Yue Guizhou, Huang Qianming, Zou Ping   

  1. College of Biology and Science, Sichuan Agricultural University, Ya'an 625014, China
  • Received: Revised: Online: Published:
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In 2008, the guaiane sesquiterpene (-)-englerin A, isolated from the genus phyllanthus engleri in East Africa, selectively inhibited the growth of renal cancer cell lines with GI50 values ranging from 1—87nm. It was found to be 1—2 orders of magnitude more potent than taxol against certain cell lines. The promising bioactivity and the structural complexity of (-)-englerin A and its analogues have attracted many organic chemists all over the world. Many studies toward the total synthesis of englerin A and its analogues were reported in three years. The article reviews the progress on the synthesis of englerin A and its analogues,We classified these syntheses according to key strategies for syntheses of englerin A and its analogues and elaboratted the characteristics of these synthetic routes. Contents 1 Introduction
2 Key strategies for syntheses of englerin A and its analogues
2.1 Ring-closing metathesis (RCM)
2.2 Gold(Ⅰ)-catalytic domino reaction
2.3 Oxopyrilium [5+2] cycloaddition
2.4 Rh(Ⅱ)-catalytic [4+3] cycloaddition
2.5 Organocatalytic [4+3] cycloaddition
2.6 Transannular epoxide opening reaction
2.7 SmI2-mediated cyclization
3 Conclusions and outlook
Key words: sesquiterpenoids, (-)-englerin A, synthesis

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[1] Ratnayake R, Covell D, Ransom T T, Gustafson K R, Beuler J A. Org. Lett., 2009, 11: 57-60
[2] Beutler J A, Ratnayake R, Covell D, Johnson T R. WO 2009088854, 2009
[3] Akee R K, Ratnayake R, McMaho J B, Beutler J A. J. Nat. Prod., 2012, 75: 459-463
[4] Schuster M, Blechert S. Angew. Chem. Int. Ed., 1997, 36: 2036-2056
[5] Nicolaou K C, Bulger P G, Sarlah D. Angew. Chem. Int. Ed., 2005, 44: 4490-4527
[6] Willot M, Radtke L, Konning D, Frohlich R, Gessner V H, Strohmann C, Christmann M. Angew. Chem. Int. Ed., 2009, 48: 9105-9108
[7] Radtke L, Willot M, Sun H, Ziegler S, Sauerland S, Strohmann C, Fröhlich R, Habenberger P, Waldmann H, Christmann M. Angew. Chem. Int. Ed., 2011, 50: 3992-4002
[8] Schreiber S L, Meyers H V, Wiberg K B. J. Am. Chem. Soc., 1986, 108: 8274-8277
[9] Jimeénez-Núñez E K, Echavarren A M. Chem. Rev., 2008, 108: 3326-3350
[10] Zhou Q, Chen X, Ma D. Angew. Chem. Int. Ed., 2010, 49: 3513-3516
[11] Jiménez-Nénez E K, Claverie C, Nieto-Oberhuber C, Echavarren A M. Angew. Chem. Int. Ed., 2006, 45: 5452-5455
[12] Jiménez-Nénez E, Molawi K, Echavarren A M. Chem. Commun., 2009, 7327-7329
[13] Peng G P, Tian G, Huang X F, Lou F C. Phytochemistry, 2003, 63: 877-881
[14] 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. Helv. Chim. Acta, 2006, 89: 1169-1175
[15] Molawi K, Delpont N, Echavarren A M. Angew. Chem. Int. Ed., 2010, 49: 3517-3519
[16] Echavarren P, Antonio M, Molawi K, Delpont N, Nicolas P R. WO 2011120886, 2011
[17] Willot M, Christmann M. Nat. Chem., 2010, 2: 519-520
[18] Singh V, Krishna U M, Vikrant, Trivedi G K. Tetrahedron, 2008, 64: 3405-3428
[19] Pellissier H. Adv. Synth. Catal., 2011, 353: 189-218
[20] Wender P A, Kogen H, Lee H Y, Munger J D, Wilhelm R S, Williams P D. J. Am. Chem. Soc., 1989, 111: 8957-8958
[21] Wender P A, Jesudason C D, Nakahira H, Tamura N, Tebbe A L, Ueno Y. J. Am. Chem. Soc., 1997, 119: 12976-12977
[22] Ali M A, Bhogal N, Findlay J B C, Fishwick C W G. J. Med. Chem., 2005, 48: 5655-5658
[23] Roethle P A, Hernandez P T, Trauner D. Org. Lett., 2006, 8: 5901-5904
[24] Li Y, Nawrat C C, Pattenden G, Winne J M. Org. Biomol. Chem., 2009, 7: 639-640
[25] Ishida K, Kusama H, Iwasawa N. J. Am. Chem. Soc., 2010, 132: 8842-8843
[26] Burns N, Witten M R, Jacobsen E N. J. Am. Chem. Soc., 2011, 133: 14578-14581
[27] Nicolaou K C, Kang Q A, Ng S Y, Chen D Y K. J. Am. Chem. Soc., 2010, 132: 8219-8222
[28] Chen K P, Chen D Y K. ChemMedChem, 2011, 6: 420-423
[29] Doyle M P, Forbes D C. Chem. Rev., 1998, 98: 911-936
[30] Maas G. Chem. Soc. Rev., 2004, 33: 183-190
[31] Padwa A, Krumpe K E. Tetrahedron, 1992, 48: 5385-5386
[32] Navickas V, Ushakov D B, Maier M E, Stroöbele M, Meyer H J. Org. Lett., 2010, 12: 3418-3421
[33] Xu J, Caro-Diaz E J E, Theodorakis E A. Org. Lett., 2010, 12: 3708-3711
[34] Harmata M, Ghosh S K, Hong X C, Wacharasindhu S, Kirchhoefer P. J. Am. Chem. Soc., 2003, 125: 2058-2059
[35] Sun B F, Wang C L, Ding R, Xu J Y, Lin G Q. Tetrahedron Lett., 2010, 52: 2155-2158
[36] Wang C L, Sun B F, Chen S G, Lin G Q, Ding R, Xu J Y, Shan Y J. Synlett, 2012, 263-266
[37] Ushakov D B, Navickas V, Ströbele M, Maichle-Mössmer C, Sasse F, Maier M E. Org. Lett., 2011, 13: 2090-2093
[38] Namy J L, Girard P, Kagan H B. New J. Chem., 1977, 1: 5-7
[39] Nicolaou K C, Ellery P S, Chen J S. Angew. Chem. Int. Ed., 2009, 48: 7140-7165
[40] Li Z, Nakashige M, Chain W J. J. Am. Chem. Soc., 2011, 133: 6553-6556
[41] Chain W J. Synlett, 2011, 2605-2608
[42] Szostak M, Procter D J. Angew. Chem. Int. Ed., 2011, 50: 7737-7739
[43] Parmar D, Price K, Spain M, Matsubara H, Bradley P A, Procter D J. J. Am. Chem. Soc., 2011, 133: 2418-2490
[44] Pouwer R H, Richard J A, Tseng C C, Chen D Y K. Chem. Asian J., 2011, 7: 22-35
[45] 卢云宇(Lu Y Y), 姚和权(Yao H Q), 孙炳峰(Sun B F). 有机化学(Chinese Journal of Organic Chemistry), 2012, 32: 1-12
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