Progress in Asymmetric Synthesis of Galanthamine-Type Alkaloids

doi:10.6023/cjoc201312002

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 852-864.DOI: 10.6023/cjoc201312002 Previous Articles Next Articles

Reviews

加兰他敏类生物碱的不对称合成研究进展

王海明^a, 陈鹏^b, 唐萌^a

a 兰州大学药学院兰州 730000;
b 吉林大学化学学院无机合成与制备化学国家重点实验室长春 130012

收稿日期:2013-12-02 修回日期:2014-01-07 发布日期:2014-02-10
通讯作者: 陈鹏，唐萌 E-mail:pengchen@jlu.edu.cn
基金资助:
国家自然科学基金（No. 21302061）、中国博士后科学基金（Nos. 2013T60318，2012M510130）和吉林省科技发展计划（No. 20140520084JH）资助项目.

Progress in Asymmetric Synthesis of Galanthamine-Type Alkaloids

Wang Haiming^a, Chen Peng^b, Tang Meng^a

a School of Pharmacy, Lanzhou University, Lanzhou 730000;
b State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012

Received:2013-12-02 Revised:2014-01-07 Published:2014-02-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21302061), the China Postdoctoral Science Foundation (Nos. 2013T60318, 2012M510130) and the Jilin Province Science and Technology Development Plan Item (No. 20140520084JH).

Galanthamine-type alkaloids are an important type of hydrodibenzofuran alkaloids. Their unique intriguing structures, significant biological activitives and pharmacological potential have attracted much attention of chemists and pharmacologists. The major challenge for their synthesis is how to construct the aryl-substituted all-carbon quaternary stereogenic center. In this paper, current strategies for asymmetric synthesis of galanthamine-type alkaloids are reviewed, and the different methods to prepare the quaternary carbon are discussed. The features of different strategies are also commented.

Key words: galanthamine, lycoramine, asymmetric synthesis, all-carbon quaternary stereogenic center

Cite this article

Wang Haiming, Chen Peng, Tang Meng. Progress in Asymmetric Synthesis of Galanthamine-Type Alkaloids[J]. Chin. J. Org. Chem., 2014, 34(5): 852-864.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Proskurnina, N. F.; Yakoleva, A. P. J. Gen. Chem. 1952, 22, 1899.

[2] (a) Han, S. Y.; Sweeney, J. E.; Bachman, E. S.; Schweiger, E. J.; Forloni, G.; Coyle, J. T.; Davis, B. M.; Joullie, M. M. Eur. J. Med. Chem. 1992, 27, 673。

(b) Marco-Contelles, J.; do Carmo Carreiras, M.; Rodriguez, C.; Villarroya, M.; Garcia, A. G. Chem. Rev. 2006, 106, 116.

[3] (a) Boers, G. M.; Kosley, R. W. Drugs Future 1996, 21, 621.

(b) Rainer, M. Drugs Today 1997, 33, 273.

(c) Mucke, H. A. M. Drugs Today 1997, 33, 259.

(d) Giacobini, E. Neurochem. Int. 1998, 32, 413.

(e) Weinstock, M. CNS Drugs 1999, 12, 307.

(f) Sramek, J. J.; Frackiewicz, E. J.; Cutler, N. R. Expert Opin. Investig. Drugs 2000, 9, 2393.

[4] Lilienfeld, S. CNS Drug Rev. 2002, 8, 159.

[5] Kondo, H.; Tomimura, K.; Ishiwata, S. J. Pharm. Soc. Jpn. 1932, 52, 433.

[6] (a) Fan, C. A.; Tu, Y. Q.; Song, Z. L.; Zhang, E.; Shi, L.; Wang, M.; Wang, B.; Zhang, S. Y. Org. Lett. 2004, 6, 4691.

(b) Hu, X. D.; Tu, Y. Q.; Zhang, E.; Gao, S.; Wang, S.; Wang, A.; Fan, C. A.; Wang, M. Org. Lett. 2006, 8, 1823.

[7] Chen, J. Q.; Xie, J. H.; Bao, D. H.; Liu, S.; Zhou, Q. L. Org. Lett. 2012, 14, 2714.

[8] Chen, P.; Bao, X.; Zhang, L. F.; Ding, M.; Han, X. J.; Li, J.; Zhang, G. B.; Tu, Y. Q.; Fan, C. A. Angew. Chem. Int. Ed. 2011, 50, 8161.

[9] (a) Parker, K. A.; Fokas, D. J. Am. Chem. Soc. 1992, 114, 9688.

(b) Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028.

(c) Taber, D. F.; Neubert, T. D.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12416.

(d) Stork, G.; Yamashita, A.; Adams, J.; Schulte, G. R.; Chesworth, R.; Miyazaki, Y.; Farmer, J. J. J. Am. Chem. Soc. 2009, 131, 11402.

(e) He, Z.-L.; Wu, Y.-L.; Hong, Y.-S.; Wu, Y.-K.; Yao, Z.-J. Total Synthesis of Natural Products—Alkaloids, Science Press, Beijing, 2009 (in Chinese).

(何子乐, 吴毓林, 洪永叁, 伍贻康, 姚祝军, 天然产物全合成荟萃——生物碱, 科学出版社, 北京, 2009.)

[10] (a) Gong, J.; Lin, G.; Sun, W.; Li, C. C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 16745.

(b) Peng, F.; Danishefsky, S. J. J. Am. Chem. Soc. 2012, 134, 18860.

(c) Lu, P.; Gu, Z.; Zakarian, A. J. Am. Chem. Soc. 2013, 135, 14552.

[11] Cha, J. Y.; Yeoman, J. T.; Reisman, S. E. J. Am. Chem. Soc. 2011, 133, 14964.

[12] (a) Marco-Contelles, J.; Perez-Mayoral, E.; van Nhien, A. N.; Postel, D. Targets Heterocycl. Syst. 2007, 11, 365.

(b) Fang, L.; Gou, S. H.; Zhang, Y. H. Chin. J. Org. Chem. 2011, 31, 286 (in Chinese).

(房雷, 苟少华, 张奕华, 有机化学, 2011, 31, 286.)

[13] Shieh, W.-C.; Carlson, J. A. J. Org. Chem. 1994, 59, 5463.

[14] Magnus, P.; Sane, N.; Fauber, B. P.; Lynch, V. J. Am. Chem. Soc. 2009, 131, 16045.

[15] (a) Kametani, T.; Sivaraman Premila, M.; Fukumoto, K. Heterocycles 1976, 4, 1111.

(b) Szewczyk, J.; Wilson, J. W.; Lewin, A. H.; Carroll, F. I. J. Heterocycl. Chem. 1995, 32, 195.

(c) Chaplin, D. A.; Johnson, N. B.; Paul, J. M.; Potter, G. A. Tetrahedron Lett. 1998, 39, 6777.

[16] (a) Barton, D. H. R.; Kirby, G. W. J. Chem. Soc. 1962, 806.

(b) Barton, D. H. R.; Kirby, G. W.; Taylor, J. B.; Thomas, G. M. J. Chem. Soc. 1963, 4545.

(c) Fuganti, C. Chim. Ind. (Milan) 1969, 51, 1254.

(d) Bhandarkar, J. G.; Kirby, G. W. J. Chem. Soc. (C) 1970, 1224.

(e) Eichhorn, J.; Takada, T.; Kita, Y.; Zenk, M. H. Phytochemistry 1998, 49, 1037.

[17] (a) Tomioka, K.; Shimizu, K.; Yamada, S.-I.; Koga, K. Heterocycles 1977, 6, 1752.

(b) Shimizu, K.; Tomioka, K.; Yamada, S.-I.; Koga, K. Heterocycles 1977, 8, 277.

(c) Shimizu, K.; Tomioka, K.; Yamada, S.-I.; Koga, K. Chem. Pharm. Bull. 1978, 26, 3765.

[18] (a) Kodama, S.; Hamashima, Y.; Nishide, K.; Node, M. Angew. Chem., Int. Ed. 2004, 43, 2659.

(b) Node, M.; Kodama, S.; Hamashima, Y.; Katoh, T.; Nishide, K.; Kajimoto, T. Chem. Pharm. Bull. 2006, 54, 1662.

[19] Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 11262.

[20] (a) Trost, B. M.; Tang, W. Angew. Chem., Int. Ed. 2002, 41, 2795.

(b) Trost, B. M.; Tang, W.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 14785.

[21] Zang, Y.; Ojima, I. J. Org. Chem. 2013, 78, 4013.

[22] Satcharoen, V.; McLean, N. J.; Kemp, S. C.; Camp, N. P.; Brown, R. C. Org. Lett. 2007, 9, 1867.

[23] Kim, Y.-J.; Tae, J. Synlett 2006, 61.

[24] Choi, J.; Kim, H.; Park, S.; Tae, J. Synlett 2013, 379.

[25] Malachowski, W. P.; Paul, T.; Phounsavath, S. J. Org. Chem. 2007, 72, 6792.

[26] Tanimoto, H.; Kato, T.; Chida, N. Tetrahedron Lett. 2007, 48, 6267.

[27] Imuta, S.; Tanimoto, H.; Momose, M. K.; Chida, N. Tetrahedron 2006, 62, 6926.

[28] Kato, T.; Tanimoto, H.; Yamada, H.; Chida, N. Heterocycles 2010, 82, 563.

加兰他敏类生物碱的不对称合成研究进展

Progress in Asymmetric Synthesis of Galanthamine-Type Alkaloids

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[2]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[3]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[4]	Tingyu Song, Ran Li, Lihua Huang, Shikun Jia, Guangjian Mei. Catalytic Asymmetric Synthesis of N—N Atropisomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1977-1990.
[5]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[6]	Ling Meng, Jun Wang. Research Progress on Synthesis of Thioflavonoids [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 873-891.
[7]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[8]	Liu-Yang Pu, Zhiyue Li, Limin Li, Yucui Ma, Min Ma, Shengquan Hu, Zhengzhi Wu. Asymmetric Synthesis of (–)-Colchicine and Its Natural Analog (–)-N-Acetylcolchicine Methyl Ether [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 313-319.
[9]	Yuanhao Mao, Yanfeng Gao, Zhiwei Miao. Research Progress on the Asymmetric Cyclization Synthesis of Seven-Membered Rings via Transition Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1904-1924.
[10]	Ting Yao, Jiayan Li, Jiaming Wang, Changgui Zhao. Recent Advances for the Construction of Seven-Membered Ring Catalyzed by N-Heterocyclic Carbenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 925-944.
[11]	Lihua Wang, Xushun Gong, Ting Lei, Shizhi Jiang. Research Progress on Asymmetric Synthesis of Flavanones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 758-769.
[12]	Xudong Hu, Xinliang Zhang, Wenbo Liu. Advances of Chiral Spiro Skeleton-Based Bisnitrogen Ligands in Transition-Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3102-3117.
[13]	Xiuliang Cheng, Dong Li, Boxuan Yang, Yumei Lin, Lei Gong. Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3335-3350.
[14]	Yiwen Su, Youquan Zou, Wenjing Xiao. Recent Advances in Photocatalytic Deracemization [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3201-3212.
[15]	Haimeng Zhu, Chao Wang, Lili Zong. Progress on Biological Activity Study and Enantioselective Synthesis of Sulfoxides [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3431-3447.