Progress in Total Syntheses of Leuconolam- Leuconoxine-Mersicarpine Alkaloids

doi:10.6023/cjoc201603030

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (7): 1447-1464.DOI: 10.6023/cjoc201603030 Previous Articles Next Articles

Reviews

Leuconolam-Leuconoxine-Mersicarpine系列单萜吲哚生物碱的全合成研究进展

耿谦^a, 李子宁^a, 吕哲^a, 梁广鑫^a,b

a. 南开大学元素有机化学国家重点实验室天津 300071;
b. 天津化学化工协同创新中心天津 300071

收稿日期:2016-03-17 修回日期:2016-04-27 发布日期:2016-05-06
通讯作者: 梁广鑫 E-mail:lianggx@nankai.edu.cn
基金资助:
国家自然科学基金（Nos.21372127，21572104）和教育部新世纪人才资助项目.

Progress in Total Syntheses of Leuconolam- Leuconoxine-Mersicarpine Alkaloids

Geng Qian^a, Li Zining^a, Lü Zhe^a, Liang Guangxin^a,b

a. State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071;
b. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071

Received:2016-03-17 Revised:2016-04-27 Published:2016-05-06
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21372127, 21572104) and the Program for New Century Excellent Talents in University.

Leuconolam-leuconoxine-mersicarpine monoterpene indole alkaloids are mainly isolated from Apocynaceae Kopsia species of plant. Though sharing the same biogenetic origin, they are a family of natural products showing incredible structural complexity and diversity. Moreover, many of them exhibit excellent bioactivities, for example, anti-inflammatory, anti-tumor activities. The progress in the total synthesis of this remarkable family of alkaloids is reviewed.

Key words: leuconolam, leuconoxine, mersicarpine, monoterpene indole alkaloid, total synthesis

Cite this article

Geng Qian, Li Zining, Lü Zhe, Liang Guangxin. Progress in Total Syntheses of Leuconolam- Leuconoxine-Mersicarpine Alkaloids[J]. Chin. J. Org. Chem., 2016, 36(7): 1447-1464.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Goh, S. H.; Ali, A. R. M. Tetrahedron Lett. 1986, 27, 2501.
(b) Hájí?ek, J.; Czech, Collect. Chem. Commun. 2011, 76, 2023.
(c) Ishikura, M.; Abe, T.; Choshi, T.; Hibino, S. Nat. Prod. Rep. 2013, 30, 694.
(d) Low, Y.-Y.; Hong, F.-J.; Lim, K.-H.; Thomas, N. F.; Kam, T.-S. J. Nat. Prod. 2014, 77, 327.
[2] (a) Kam, T.-S.; Subramaniam, G.; Lim, K.-H.; Choo, Y.-M. Tetrahedron Lett. 2004, 45, 5995.
(b) Gan, C.-Y.; Low, Y.-Y.; Thomas N. F.; Kam, T.-S. J. Nat. Prod. 2013, 76, 957.
[3] Abe F.; Yamauchi, T. Phytochemistry 1994, 35, 169.
[4] (a) Feng, T.; Cai, X.-H.; Zhao, P.-J.; Du, Z.-Z.; Li W.-Q.; Luo, X.-D. Planta Med. 2009, 75, 1537.
(b) Gan, C.-Y.; Low, Y.-Y.; Thomas N. F.; Kam, T.-S. J. Nat. Prod. 2013, 76, 957.
[5] Feng, T.; Cai, X.-H.; Liu, Y.-P.; Li, Y.; Wang, Y.-Y.; Luo, X.-D J. Nat. Prod. 2010, 73, 22.
[6] Goh, S. H.; Wei C.; Ali, A. R. M. Tetrahedron Lett. 1984, 25, 3483.
[7] For selected syntheses of other alkaloids bearing dearomatized indole moiety, see:
(a) Han S.; Movassaghi, M. J. Am. Chem. Soc. 2011, 133, 10768.
(b) Zhang, X.; Mu, T.; Zhan, F.; Ma L.; Liang, G. Angew. Chem., Int. Ed. 2011, 50, 6164.
(c) Zhan, F.; Liang, G. Angew. Chem., Int. Ed. 2013, 52, 1266.
(d) Li, S.; Han, J.; Li, A. Acta Chim. Sinica 2013, 71, 295.
(e) Sun, Y.; Li, R.; Zhang W.; Li, A. Angew. Chem., Int. Ed. 2013, 52, 9201.
(f) Sun, Y.; Chen, P.; Zhang, D.; Baunach, M.; Hertweck, C.; Li, A. Angew. Chem., Int. Ed. 2014, 53, 9012.
[8] Magolan, J.; Carson C. A.; Kerr, M. A. Org. Lett. 2008, 10, 1437.
[9] Nakajima, R.; Ogino, T.; Yokoshima S.; Fukuyama, T. J. Am. Chem. Soc. 2010, 132, 1236.
[10] (a) Iwama, Y.; Okano, K.; Sugimoto, K.; Tokuyama, H. Org. Lett. 2012, 14, 2320.
(b) Iwama, Y.; Okano, K.; Sugimoto, K.; Tokuyama, H. Chem. Eur. J. 2013, 19, 9325.
[11] (a) Xu, Z.; Wang, Q.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 19127.
(b) Xu, Z.; Wang Q.; Zhu, J. J. Am. Chem. Soc. 2015, 137, 6712.
[12] (a) Lv, Z.; Li, Z.; Liang, G. Org. Lett. 2014, 16, 1653.
(b) Li, Z.; Geng, Q.; Lv, Z.; Pritchett, B. P.; Baba, K.; Numajiri, Y.; Stoltz, B. M.; Liang, G. Org. Chem. Front. 2015, 2, 236.
[13] Yang, Y.; Bai, Y.; Sun, S.; Dai, M. Org. Lett. 2014, 16, 6216.
[14] Biechy, A.; Zard, S. Z. Org. Lett. 2009, 11, 2800.
[15] (a) Zhong, X.; Li Y.; Han, F.-S. Chem. Eur. J. 2012, 18, 9784.
(b) Zhong, X.; Qi, S.; Li, Y.; Han, F.-S. Tetrahedron 2015, 71, 3734.
[16] Pfaffenbach, M.; Gaich, T. Eur. J. Org. Chem. 2015, 2015, 3427.
[17] Umehara, A.; Ueda, H.; Tokuyama, H. Org. Lett. 2014, 16, 2526.
[18] Higuchi, K.; Suzuki, S.; Ueda, R.; Oshima, N.; Kobayashi, E.; Tayu, M.; Kawasaki, T. Org. Lett. 2015, 17, 154.
[19] Pfaffenbach, M.; Gaich, T. Chem. Eur. J. 2015, 21, 6355.
[20] (a) Banwell, M. G.; Beck, D. A. S.; Willis, A. C. ARKIVOC 2006, (iii), 163.
(b) Izgu, E. C.; Hoye, T. R. Chem. Sci. 2013, 4, 2262.
[21] For representative total syntheses of rhazinilam, see:
(a) Ratcliffe, A. H.; Smith, G. F.; Smith, G. N. Tetrahedron Lett. 1973, 14, 5179.
(b) Magnus, P.; Rainey, T. Tetrahedron 2001, 57, 8647.
(c) Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2000, 122, 6321.
(d) Johnson, J. A.; Li, N.; Sames, D. J. Am. Chem. Soc. 2002, 124, 6900.
(e) Bowie, A. L.; Hughes, C. C.; Trauner, D. Org. Lett. 2005, 7, 5207.
(f) Liu, Z.; Wasmuth, A. S.; Nelson, S. G. J. Am. Chem. Soc. 2006, 128, 10352.
(g) Bowie, A. L.; Trauner, D. J. Org. Chem. 2009, 74, 1581.
(h) Gu, Z.; Zakarian, A. Org. Lett. 2010, 12, 4224.
(i) McMurray, L.; Beck, E. M.; Gaunt, M. Angew. Chem., Int. Ed. 2012, 51, 9288.
(j) Gualtierotti, J.-B.; Pasche, D.; Wang Q.; Zhu, J. Angew. Chem., Int. Ed. 2014, 53, 9926.
[22] Décor, A.; Bellocq, D.; Thoison, O.; Lekieffre, N.; Chiaroni, A.; Ouazzani, J.; Cresteil, T.; Guéritte, F.; Baudoin, O. Bioorg. Med. Chem. 2006, 14, 1558.
[23] Li, Z.; Liang, G. Tetrahedron Lett. 2013, 54, 242. (a) Li, H.; Cheng, B.; Boonnak, N.; Padwa, A. Tetrahedron Lett. 2011, 67, 9829.
(b) Li, H.; Bonderoff, S. A.; Cheng, B.; Padwa, A. J. Org. Chem. 2014, 79, 392.

Leuconolam-Leuconoxine-Mersicarpine系列单萜吲哚生物碱的全合成研究进展

Progress in Total Syntheses of Leuconolam- Leuconoxine-Mersicarpine Alkaloids

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xingzhou Liu, Mingjia Yu, Jianhua Liang. Research Progress on the Synthesis of Protoberberine Skeleton and Its Anti-inflammatory Activity [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1325-1340.
[2]	Jingping Hu, Wenqing Chen, Yuyang Jiang, Jing Xu. Synthesis of Tetracyclic Core Structure of Daphnezomines A and B [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 171-177.
[3]	Xiangkai Kong, Yipeng Zhang, Lingjing Dang, Wen Chen, Hongbin Zhang. Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2728-2744.
[4]	Ran Gao, Weisheng Tian. Synthesis of Azedarachol and 2α,3α,20R-Trihydroxypregnane-16β-methacrylate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2521-2526.
[5]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.
[6]	Jun Zhao, Jian Xiao, Yawen Wang, Yu Peng. Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2933-2945.
[7]	Minxin Li, Qiuping Zou, Wenrong Du, Jinchun Gao, Yanping Li, Zewei Mao. Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3292-3296.
[8]	Jian Xiao, Yu Peng, Wei-Dong Z. Li. Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2636-2649.
[9]	Xifei Yan, Jianfeng Zheng, Wei-Dong Z. Li. Studies on the Chemical Synthesis of Natural Drugs Berberine [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2217-2227.
[10]	Gang Yang, Xiangyu Feng, Congcong Han, Yang Chen, Shuzhong He. Synthesis of the ABC Ring System of Wallichanol Natural Product [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 726-730.
[11]	Ding Ma, Junli Ao, Naifeng Hu, Guangxin Liang. Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 553-566.
[12]	Lu Guo, Pingping Tang. Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3816-3825.
[13]	Han Jilai, Tang Meilin, Sun Xun. Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1571-1577.
[14]	Dong Wei, Wang Xin, Ge Zemei, He Fang, Li Runtao. Efficient Synthesis of Wogonin [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1725-1730.
[15]	Xie Tao, He Haibing, Gao Shuanhu. Synthetic Progress of Polycyclic Xanthone [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 551-562.