Total Synthesis of Racemic (±)-Parvistemonine A

doi:10.6023/cjoc201901010

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 2094-2098.DOI: 10.6023/cjoc201901010 Previous Articles Next Articles

Notes

(±)-Parvistemonine A的全合成

马开庆^a, 任虎斌^a,b, 吴晓晓^a, 钞建斌^c, 秦雪梅^a

a 山西大学中医药现代研究中心太原 030006;
b 山西大学化学化工学院太原 030006;
c 山西大学大型仪器中心太原 030006

收稿日期:2019-01-07 修回日期:2019-02-12 发布日期:2019-03-08
通讯作者: 马开庆 E-mail:makaiqing@sxu.edu.cn
基金资助:
山西省回国留学人员科研资助基金（No.2015-020）和山西省高等学校科技创新基金（No.2016115）资助项目.

Total Synthesis of Racemic (±)-Parvistemonine A

Ma Kaiqing^a, Ren Hubin^a,b, Wu Xiaoxiao^a, Chao Jianbin^c, Qin Xuemei^a

a Modern Research Center for Traditional Chinese Medicine, Shanxi University, Taiyuan 030006;
b College of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006;
c Scientific Instrument Center, Shanxi University, Taiyuan 030006

Received:2019-01-07 Revised:2019-02-12 Published:2019-03-08
Contact: 10.6023/cjoc201901010 E-mail:makaiqing@sxu.edu.cn
Supported by:
Project supported by the Shanxi Scholarship Council of China (No. 2015-020) and the Science and Technology Innovation Project of Shanxi Province (No. 2016115).

1. Total Synthesis of Racemic (±)-Parvistemonine A.PDF(1004KB)

Abstract

Parvistemonine A was isolated from Stemona parviflora. The total synthesis of racemic parvistemonine A was completed in 6 steps for the first time, employing compound 7 as the starting material. The synthetic strategy features a tandem Friedel-Crafts cyclization and lactonization, Vilsmeier-Haack and Julia-Kocienski olefination. This study laid the foundation for the synthesis of the parvistemonine A derivative and its biological activity research.

Key words: natural product, stemona alkaloids, parvistemonine A, chemical synthesis

Cite this article

Ma Kaiqing, Ren Hubin, Wu Xiaoxiao, Chao Jianbin, Qin Xuemei. Total Synthesis of Racemic (±)-Parvistemonine A[J]. Chin. J. Org. Chem., 2019, 39(7): 2094-2098.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Pilli, R. A.; Rosso, G. B.; de Oliveira, M. C. F. Nat. Prod. Rep. 2010, 27, 1908.
[2] Pilli, R. A.; de Oliveira, M. C. F. Nat. Prod. Rep. 2000, 17, 117.
[3] Frankowski, K. J.; Setola, V.; Evans, J. M.; Neuenswander, B.; Roth, B. L.; Aube, J. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 6727.
[4] Lin, L.-G.; Zhong, Q.-X.; Cheng, T.-Y.; Tang, C.-P.; Ke, C.-Q.; Lin, G.; Ye, Y. J. Nat. Prod. 2006, 69, 1051.
[5] Hu, Z.-X.; Tang, H.-Y.; Guo, J.; Aisa, H. A.; Zhang, Y.; Hao, X.-J. Tetrahedron 2018, 75, 1711.
[6] Li, Y.-Y.; Wang, Y.-Y.; Taniguchi, T.; Kawakami, T.; Baba, T.; Ishibashi, H.; Mukaida, N. Int. J. Cancer 2010, 127, 474.
[7] Chanmahasathien, W.; Ohnuma, S.; Ambudkar, S. V.; Limtrakul, P. Planta Med. 2011, 77, 1990.
[8] Wang, Y.-J.; Zhao, H.-D.; Zhu, C.-F.; Li, J.; Xie, H.-J.; Chen, Y.-X. J. Cancer 2017, 8, 1103.
[9] Alibes, R.; Figueredo M. Eur. J. Org. Chem. 2009, 15, 2421.
[10] Brito, G. A.; Pirovani, R. V. Org. Prep. Proced. Int. 2018, 50, 245.
[11] Huang, S.-Z.; Kong, F.-D.; Ma, Q.-Y.; Guo, Z.-K.; Zhou, L.-M.; Wang, Q.; Dai, H.-F.; Zhao, Y.-X. J. Nat. Prod. 2016, 79, 2599.
[12] Ma, K.-Q.; Yin, X.-L.; Dai, M.-J. Angew. Chem., Int. Ed. 2018, 57, 15209.
[13] Fang, J.; Brewer, M. Org. Lett. 2018, 20, 7384.
[14] Zhao, K.; Wang, S.; Zhan, X. P.; Liu, Z. L.; Mao, Z. M. Chin. J. Org. Chem. 2017, 37, 943(in Chinese). (赵凯, 王帅, 詹晓平, 刘增路, 毛振民, 有机化学, 2017, 37, 943.)
[15] Al'bina, I. M.; Ivanov, A. V.; Skital'tseva, E. V.; Igor'A, U.; Vasil'tsov, A. M.; Trofimov, B. A. Synthesis 2009, 587.
[16] Ren, R. G.; Mao, Z. Y.; Wei, B. G.; Lin, G. Q. Chin. J. Org. Chem. 2015, 35, 2313(in Chinese). (任荣国, 毛(艹卓)亚, 魏邦国, 林国强, 有机化学, 2015, 35, 2313.)
[17] Dussart, N.; Trinh, H. V.; Gueyrard, D. Org. Lett. 2016, 18, 4790.

(±)-Parvistemonine A的全合成

Total Synthesis of Racemic (±)-Parvistemonine A

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.
[2]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[3]	Xiurong Wu, Chaojiang Xiao, Yi Shen, Hongxia Tang, Junyi Zhu, Bei Jiang. Research Progress on Antimalarial Natural Sesquiterpenoids from Plants from 1972 to 2022 [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2764-2789.
[4]	Junying Zhang, Xiaojing Zhao, Ganpeng Li, Yonghui He. Electrochemical Synthesis of Masked Organoboronic Acids RB(dan) at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1815-1823.
[5]	Yongzhou Pan, Xiujin Meng, Yingchun Wang, Muxue He. Recent Progress in Electrochemical Fixation of CO₂ to Construct Carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1416-1434.
[6]	Tianyang Wang, Yan-Mei Li. Progress on the Synthesis and Activity of Cyclic Dinucleotides as Stimulator of Interferon Gene (STING) Agonists [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 892-913.
[7]	Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei. Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 756-762.
[8]	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.
[9]	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.
[10]	Liangcai Yao, Jinghan Gui. Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2703-2714.
[11]	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.
[12]	Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang, Pan Han, Linhai Jing. Synthesis of Nitrile via Electrochemical Appel Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2229-2235.
[13]	Fasheng Shi, Shengwen Wang, Huan Xu, Xingxing Lu, Xinling Yang, Tengda Sun, Changkai Wang, Xiaoming Zhang, Qing Yang, Yun Ling. Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2106-2116.
[14]	Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam 3-Hydroxycombamide I [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1557-1561.
[15]	Jie Luo, Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam Clifednamide K [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1224-1228.