Natural Products and Bioprospecting    2012, Vol. 2 Issue (6) : 255-257     DOI: 10.1007/s13659-012-0084-2
Short Communication |
One-step synthesis of Lycopodium alkaloid(-)-huperzine W via Suzuki-Miyaura coupling
Tao XUa,b, Shi-Zhi JIANGa, Huai-Rong LUOa, Yu-Rong YANGa
a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China
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Abstract  The first total synthesis of(-)-huperzine W(1) has been achieved. Key element of the synthesis is a highly convergent assemblage for the two rings system of target molecule utilizing an efficient Suzuki-Miyaura coupling reaction between chiral iodide 2 and 2-allylpyrrolidinone 4. Evaluation of the AchE inhibition of synthetic huperzine W was also carried out.
Keywords total synthesis      huperzine W      Lycopodium alkaloids     
Fund:We would like to thank the National Natural Science of China(No. 20802084, 21072200), Programs of "One Hundred Talented People" and "Western Light" Joint Scholar of Chinese Academy of Sciences for financial support.
Issue Date: 11 February 2018
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Tao XU,Shi-Zhi JIANG,Huai-Rong LUO, et al. One-step synthesis of Lycopodium alkaloid(-)-huperzine W via Suzuki-Miyaura coupling[J]. Natural Products and Bioprospecting, 2012, 2(6): 255-257.
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http://npb.kib.ac.cn/EN/10.1007/s13659-012-0084-2     OR     http://npb.kib.ac.cn/EN/Y2012/V2/I6/255
[1] (a) Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752; (b) Hirasawa, Y.; Kobayashi, J.; Morita, H. Heterocycles 2009, 77, 679; (c) Kitajima, M.; Takayama, H. Top. Curr. Chem. 2012, 309, 1.
[2] (a) Ge, H. M.; Zhang, L. D.; Tan, R. X.; Yao, Z. J. J. Am. Chem. Soc. 2012, 134, 12323; (b) Nishimura, T.; Unni, A. K.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2011, 133, 418; (c) Zhang, X. M.; Tu, Y. Q.; Zhang, F. M.; Shao, H.; Meng, X. Angew. Chem. Int. Ed. 2011, 50, 3916; (d) Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 9594; (e) Nilsson, B. L.; Overman, L. E.; Alaniz, J. R.; Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 11297; (f) Kozak, J. A.; Dake, G. R. Angew. Chem. Int. Ed. 2008, 47, 4221; (g) Bisai, A.; West, S. P.; Sarpong, R. J. Am. Chem. Soc. 2008, 130, 7222.
[3] (a) Yang, Y. R.; Shen, L.; Wei, K.; Zhao, Q. S. J. Org. Chem. 2010, 75, 1317; (b) Yang, Y. R.; Lai, Z. W.; Shen, L.; Huang, J. Z.; Wu, X. D.; Yin, J. L.; Wei, K. Org. Lett. 2010, 12, 3430; (c) Yang, Y. R.; Shen, L.; Huang, J. Z.; Xu, T.; Wei, K. J. Org. Chem. 2011, 76, 3684.
[4] Tan, C. H.; Ma, X. Q.; Chen, G. F.; Jiang, S. H.; Zhu, D. Y. Chin. Chem. Lett. 2002, 13, 331.
[5] (a) Harayama, T.; Takatani, M.; Inubushi, Y. Chem. Pharm. Bull. 1980, 28, 2394; (b) Li, H.; Wang, W.; Lei, X. Angew. Chem. Int. Ed. 2012, 51, 491.
[6] (a) Morita, H.; Kobayashi, J. J. Org. Chem. 2002, 67, 5378; (b) Harayama, T.; Ohtani, M.; Oki, M.; Inubushi, Y. J. Chem. Soc. Chem. Comm. 1974, 827.
[7] Chandra, A.; Pigza, J. A.; Han, J. S.; Mutnick, D.; Johnston, J. N. J. Am. Chem. Soc. 2009, 131, 3470.
[8] Ding, R.; Sun, B. F.; Lin, G. Q. Org. Lett. 2012, 14, 4446.
[9] (a) Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314; (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2001, 40, 4544.
[10] (a) Liu, K. M.; Chau, C. M.; Sha, C. K. Chem. Comm. 2008, 1, 91; (b) Ohmura, N.; Nakamura, A.; Hamasaki, A.; Tokunaga, M. Eur. J. Org. Chem. 2008, 30, 5042.
[11] Caine, D.; Procter, K.; Cassell, R. A. J. Org. Chem. 1984, 49, 2647.
[12] Prof. Huai-Rong Luo at Kunming Institute of Botany performed the experiments.
[13] Ellman, G. L.; Courtney, K. D.; Valentino, A., Jr.; Feathertone, R. M. Biochem. Pharmacol. 1961, 7, 88-95.
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