SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 10: 3289 - 3299

DOI: https://doi.org/10.6023/cjoc202003014

综述与进展

天然产物Gracilioethers和Hippolachnin A的合成研究进展

  • 吴璟华 ,
  • 王诚 ,
  • 陈鹏全 ,
  • 马志强
展开
  • 华南理工大学化学与化工学院 广东省功能分子工程重点实验室 广州 510641

收稿日期: 2020-03-06

  修回日期: 2020-04-08

  网络出版日期: 2020-04-17

基金资助

国家重点研发计划（No.2016YFA0602900）、广州市科技计划（No.201707010073）和国家自然科学基金（Nos.21672073，21871098）资助项目.

收起

Synthetic Progress of Natural Products Gracilioethers and Hippolachnin A

  • Wu Jinghua ,
  • Wang Cheng ,
  • Chen Pengquan ,
  • Ma Zhiqiang
Expand
  • Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Guangzhou 510641

Received date: 2020-03-06

  Revised date: 2020-04-08

  Online published: 2020-04-17

Supported by

Project supported by the National Program on Key Research Project (No. 2016YFA0602900), the Science and Technology Program of Guangzhou City (No. 201707010073) and the National Natural Science Foundation of China (Nos. 21672073, 21871098).

Fold

摘要

Gracilioether家族天然产物与hippolachnin A都是从海洋海绵中分离得到的.Gracilioether家族天然产物具有良好的抗疟疾活性，而hippolachnin A具有良好的抗菌活性.它们有趣的结构和良好的生物活性吸引了化学家的关注.按照合成的策略分类，概括了gracilioether家族中具有三环骨架结构的天然产物和hippolachnin A的全合成研究.

关键词： gracilioether; hippolachnin A; 天然产物; 全合成

本文引用格式

吴璟华 , 王诚 , 陈鹏全 , 马志强 . 天然产物Gracilioethers和Hippolachnin A的合成研究进展[J]. 有机化学, 2020 , 40(10) : 3289 -3299 . DOI: 10.6023/cjoc202003014

Abstract

Gracilioethers and hippolachnin A were isolated from marine sponge. Gracilioethers showed antimalarial activity while hippolachnin A exhibited strong antifungal activity. Their fascinating structures and outstanding biological activities have attracted attentions from chemists. Progress on the synthesis of gracilioethers with tricyclic skeleton and hippolachnin A are reviewed in terms of the key strategies employed.

Key words： gracilioether; hippolachnin A; natural product; total synthesis

参考文献

[1] Cragg, G. M.; Newman, D. J. Biochim. Biophys. Acta, Gen. Subj. 2013, 1830, 3670.
[2] Ueoka, R.; Nakao, Y.; Kawatsu, S.; Yaegashi, J.; Matsumoto, Y.; Matsunaga, S.; Furihata, K.; Soest, R. W. M. V.; Fusetani, N. J. Org. Chem. 2009, 74, 4203.
[3] Festa, C.; Lauro, G.; De Marino, S.; D'Auria, M. V.; Monti, M. C.; Casapullo, A.; D'Amore, C.; Renga, B.; Mencarelli, A.; Petek, S.; Bifulco, G.; Fiorucci, S.; Zampella, A. J. Med. Chem. 2012, 55, 8303.
[4] (a) Festa, S.; De Marino, S.; D'Auria, M. V.; Deharo, E.; Gonzalez, G.; Deyssard, C.; Petek, S.; Bifulco, G.; Zampella, A. Tetrahedron 2012, 68, 10157.
(b) Festa, C.; D'Amore, C.; Renga, B.; Lauro, G.; De Marino, S.; D'Auria, M. V.; Bifulco, G.; Zampella, A.; Fiorucci, S. Mar. Drugs 2013, 11, 2314.
[5] Piao, S.; Song, Y.; Jiao, W.; Yang, F.; Liu, X.; Chen, W.; Han, B.; Lin, H. Org. Lett. 2013, 15, 3526.
[6] (a) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449.
(b) Poplata, S.; Tröster, A.; Zou, Y.-Q.; Bach, T. Chem. Rev. 2016, 116, 9748.
(c) Salomon, R. G. Tetrahedron 1983, 39, 485.
[7] Rasik, C. M.; Brown, M. K. Angew. Chem., Int. Ed. 2014, 53, 14522.
[8] Ruider, S. A.; Sandmeier, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 2378.
[9] Ruider, S. A.; Carreira, E. M. Org. Lett. 2016, 18, 220.
[10] McCallum, M. E.; Rasik, C. M.; Wood, J. L.; Brown, M. K. J. Am. Chem. Soc. 2016, 138, 2437.
[11] Xu, Z. J.; Wu, Y. Chem.-Eur. J. 2017, 23, 2026.
[12] Li, Q.; Zhao, K.; Peuronen, A.; Rissanen, K.; Enders, D.; Tang, Y. J. Am. Chem. Soc. 2018, 140, 1937.
[13] Shen, X.; Peng, X.; Wong, H. N. C. Org. Lett. 2016, 18, 1032.
[14] Winter, N.; Trauner, D. J. Am. Chem. Soc. 2017, 139, 11706.
[15] Datta, R.; Ghosh, S. J. Org. Chem. 2017, 82, 7675.
[16] (a) Rasik, C. M.; Brown M. K. J. Am. Chem. Soc. 2013, 135, 1673.
(b) Rasik, C. M.; Brown, M. K. Synlett 2014, 760.
(c) Wang, Y.; Wei, D.; Li, Z.; Zhu, Y.; Tang, M. J. Phys. Chem. A 2014, 118, 4288.
(d) Rasik, C. M.; Hong, Y. J.; Tantillo, D. J.; Brown, M. K. Org. Lett. 2014, 16, 5168.
(e) Huston, R.; Rey, M.; Dreiding, A. S. Helv. Chim. Acta 1982, 65, 1563.
(f) Nelson, S. G.; Dura, R. D.; Peelen, T. J. Org. React. 2012, 82, 471.
(g) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Org. Chem. 1998, 63, 8380.
[17] (a) Godula, K. Science 2006, 312, 67.
(b) Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976.
(c) Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362.
[18] (a) Chen, M. S.; White, M. C. Science 2007, 318, 783.
(b) Bigi, M. A.; Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2012, 134, 9721.
(c) Shi, G.; Zhang, Y. Adv. Synth. Catal. 2014, 356, 1419.
[19] (a) Song, L.; Yao, H.; Zhu, L.; Tong, R. Org. Lett. 2013, 15, 6.
(b) Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717.
[20] (a) Dias, E. L.; Brookhart, M.; White, P. S. Chem. Commun. 2001, 423.
(b) Gao, H.; Zhang, J. Chem.-Eur. J. 2012, 18, 2777.
[21] (a) Smith, C. D. J. Am. Chem. Soc. 1966, 88, 4273.
(b) Tabushi, I.; Yamamura, K.; Yoshida, Z. J. Am. Chem. Soc. 1972, 94, 787.
(c) Petrov, V. A.; Vasil'ev, N. V. Curr. Org. Synth. 2006, 3, 215.
[22] (a) Osberger, T. J.; White, M. C. J. Am. Chem. Soc. 2014, 136, 11176.
(b) Ammann, S. E.; Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2014, 136, 10834.
(c) Malik, M.; Witkowski, G.; Jaroz, S. Org. Lett. 2014, 16, 3816.
(d) White, M. C. J. Am. Chem. Soc. 2013, 135, 14052.
[23] Morrill, L. A.; Susick, R. B.; Chari, J. V.; Garg, N. K. J. Am. Chem. Soc. 2019, 141, 12423.
[24] Kiyama, M.; Isoda, Y.; Nishimoto, M.; Kobayashi, A.; Togawa, D.; Hirao, N.; Kuboki, A.; Ohira, S.; Tetrahedron Lett. 2005, 46, 7483.
[25] Fu, C.; Ma, S. Eur. J. Org. Chem. 2005, 2005, 3942.
[26] (a) Blay, G.; Garcia, B.; Molina, E.; Pedro, J. R. Org. Lett. 2005, 7, 3291.
(b) Paquette, L. A.; Green, K. E.; Gleiter, R.; Schäfer, W.; Gallucci, J. C. J. Am. Chem. Soc. 1984, 106, 8232.
[27] Dauben, W. G.; Koch, K.; Smith, S. L.; Chapman, O. L. J. Am. Chem. Soc. 1963, 85, 2616.
[28] Reetz, M. T.; Chatziiosifidis, I.; Schwellnus, K. Angew. Chem. 1981, 93, 716.
[29] (a) RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986.
(b) RajanBabu, T. V.; Nugent, W. A.; Beattie, M. S. J. Am. Chem. Soc. 1990, 112, 6408.
(c) RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1989, 111, 4525.
(d) Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561.
Options
文章导航

/

〈 〉