Enantioselective Construction of the Pyridine-Fused Chiral Bicyclo- [3.3.1]nonane Skeleton of Huperzine A and Its Analogues

doi:10.6023/cjoc202105059

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 4021-4027.DOI: 10.6023/cjoc202105059 Previous Articles Next Articles

Special Issue: 南开大学化学学科创立100周年；热点论文虚拟合集

ARTICLES

石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的不对称构建

宾怀玉, 程立, 杨小会, 谢建华^*(), 周其林

南开大学化学学院元素有机化学国家重点实验室天津 300071

收稿日期:2021-05-31 修回日期:2021-07-07 发布日期:2021-07-19
通讯作者: 谢建华
基金资助:
国家自然科学基金(21871152); 国家自然科学基金(92056105); 国家自然科学基金(21532003); 国家自然科学基金(21790332)

Enantioselective Construction of the Pyridine-Fused Chiral Bicyclo- [3.3.1]nonane Skeleton of Huperzine A and Its Analogues

Huaiyu Bin, Li Cheng, Xiaohui Yang, Jianhua Xie(), Qilin Zhou

State Key Laboratory and Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Received:2021-05-31 Revised:2021-07-07 Published:2021-07-19
Contact: Jianhua Xie
Supported by:
National Natural Science Foundation of China(21871152); National Natural Science Foundation of China(92056105); National Natural Science Foundation of China(21532003); National Natural Science Foundation of China(21790332)

1. .pdf(1968KB)

Abstract

A concise strategy for the enantioselective construction of the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton of (+)-huperzine A and its nanlogues was reported. The key features of this strategy are the catalytic asymmetric hydrogenation of an exocyclic γ,δ-unsaturated β-ketoester via dynamic kinetic resolution combined with an intramolecular arylation as the key steps to constuct the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton. This strategy provides a concise and rapid approach to the chiral core structure of huperzine A and its nanlogues from the known starting materials (5 steps and 17.4% overall yield).

Key words: arylation, asymmetric hydrogenation, bicyclo[3.3.1]nonane skeleton, huperzine A, unsaturated ketoester

Cite this article

Huaiyu Bin, Li Cheng, Xiaohui Yang, Jianhua Xie, Qilin Zhou. Enantioselective Construction of the Pyridine-Fused Chiral Bicyclo- [3.3.1]nonane Skeleton of Huperzine A and Its Analogues[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4021-4027.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

Figure 1. Structures of huperzine A and its analogues

Scheme 1. Representative strategies for enantioselective construction of pyridine-fused chiral bicyclo[3.3.1]nonane skeleton of huperzine A

Scheme 2. Retrosynthetic analysis of enantioselective construction of the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton of huperzine A and analogues

Scheme 3. Enantioselective synthesis of unsaturated cyclic β-hydoxy ester (+)-3 and its catalytic hydrogenation

Scheme 4. Enantioselective synthesis of ketoester (+)-1

References 17

[1]	(a) Siengalewicz, P.; Mulzer, J.; Rinner, U. In The Alkaloids: Chemistry and Biology, Ed.: Knölker, H.-J., Academic Press, Cambridge, MA, 2013, Vol. 72, pp. 1-151.
	(b) Ma, X. Q.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752. doi: 10.1039/b409720n
	(c) Xiao, C.; Gao, L.; Wang, J.; Miao, Y.; Fan, H. Chin. J. Org. Chem. 2017, 37, 810. (in Chinese) doi: 10.6023/cjoc201611032
	(肖春霞, 曹林, 王佳, 苗银龙, 范华芳, 有机化学, 2017, 37, 810.) doi: 10.6023/cjoc201611032
[2]	(a) Herzon, S. B.; Tun, M. K. M. J. Exp. Pharmacol. 2012, 4, 113.
	(b) Qian, Z. M.; Ke, Y. Front. Aging Neurosci. 2014, 6, 216.
[3]	(a) Wang, L.-L.; Hao, L.-J.; Zhou, Z.-B.; Zhu, X.-L.; Shi, Z.-H.; Miyamoto, T.; Pan, K. Phytochemistry 2018, 154, 63. doi: 10.1016/j.phytochem.2018.06.016 pmid: 23941108
	(b) Zhang, D.-B.; Chen, J.-J.; Song, Q.-Y.; Zhang, L.; Gao, K. Molecules 2014, 19, 9999. doi: 10.3390/molecules19079999 pmid: 23941108
	(c) Tang, Y.; Fu, Y.; Xiong, J.; Li, M.; Ma, G.-L.; Yang, G.-X.; Wei, B.-G.; Zhao, Y.; Zhang, H.-Y.; Hu, J.-F. J. Nat. Prod. 2013, 76, 1475. doi: 10.1021/np4003355 pmid: 23941108
	(d) Yin, S.; Fan, C.-Q.; Wang, X.-N.; Yue, J.-M. Helv. Chem. Acta 2006, 89, 138. doi: 10.1002/(ISSN)1522-2675 pmid: 23941108
[4]	(a) Bai, D.-L.; Tang, X.-C.; He, X.-C. Curr. Med. Chem. 2000, 7, 355. pmid: 10637369
	(b) Ma, X.; Tan, C.; Zhu, D.; Gang, D.-R. J. Ethnopharmacol. 2006, 104, 54. doi: 10.1016/j.jep.2005.08.042 pmid: 10637369
[5]	Zheng, S.; Yu, C.; Shen, Z. Chin. J. Org. Chem. 2013, 33, 2261. (in Chinese) doi: 10.6023/cjoc201306006
	(郑书岩, 郁春辉, 沈征武, 有机化学, 2013, 33, 2261.) doi: 10.6023/cjoc201306006
[6]	Qian, L.-G.; Ji, R.-Y. Tetrahedron Lett. 1989, 30, 2089. doi: 10.1016/S0040-4039(01)93719-0
[7]	Xia, Y.; Kozikowshi, A. P. J. Am. Chem. Soc. 1989, 111, 4166. doi: 10.1021/ja00194a004
[8]	(a) Chen, W.-P.; Yang, F.-Q. Chin. J. Med. Chem. 1995, 15, 10. (in Chinese)
	(陈卫平, 杨福秋, 中国药物化学杂志, 1995, 15, 10.)
	(b) Kaneko, S.; Yoshino, T.; Katoh, T.; Terashima, S. Heterocycles 1997, 46, 27. doi: 10.3987/COM-96-S4
	(c) Kaneko, S.; Yoshino, T.; Katoh, T.; Terashima, S. Tetrahedron 1998, 54, 5471. doi: 10.1016/S0040-4020(98)00227-0
	(d) Pan, Q.-B.; Ma, D.-W. Chin. J. Chem. 2003, 21, 793. doi: 10.1002/cjoc.20030210716
	(e) Ding, X.-H.; Li, X.; Liu, D.; Cui, W.-C.; Ju, X.; Wang, S.-Z.; Yao, Z.-J. Tetrahedron 2012, 68, 6240. doi: 10.1016/j.tet.2012.05.061
[9]	(a) Kozikowski, A.P.; Campiani, G.; Aagaard, P.; Mckinney, M. J. Chem. Soc., hem. Commun. 1993, 10, 860.
	(b) Campiano, G.; Sun, L. Q.; Kozikowski, A. P. J. Org. Chem. 1993, 58, 7660. doi: 10.1021/jo00079a008
[10]	(a) Kaneko, S.; Yoshino, T.; Katoh, T.; Terashima, S. Tetrahedron: Asymmetry 1997, 8, 829. doi: 10.1016/S0957-4166(97)00048-7
	(b) He, X.-C.; Wang, B.; Bai, D.-L. Tetrahedron Lett. 1998, 39, 411. doi: 10.1016/S0040-4039(97)10535-4
	(c) Chassaing, C.; Hanudrechy, A.; Langlois, Y. Tetrahedron Lett. 1999, 40, 8805. doi: 10.1016/S0040-4039(99)01874-2
	(d) He, X.-C.; Wang, B.; Yu, G, Bai, D. Tetrahedron: Asymmetry 2001, 12, 3213. doi: 10.1016/S0957-4166(02)00006-X
	(e) Tudhope, S. R.; Bellamy, J. A.; Ball, A.; Rajasekar, D.; Azadi-Ardakani, M.; Meera, H. S.; Gnanadeepam, J. M.; Saiganesh, R.; Gibson, F.; He, L.; Behrens, C. H.; Underiner, G.; Marfurt, J.; Favre, N. Org. Process Res. Dev. 2012, 16, 635. doi: 10.1021/op200360b
	(f) Lin, C.-F.; Chien, C.-W.; Ojima, I. Org. Chem. Front. 2014, 1, 1062. doi: 10.1039/C4QO00180J
[11]	Tun, M. K. M.; Wüstmann, D.; Herzon, S. B. Chem. Sci. 2011, 2, 2251. doi: 10.1039/c1sc00455g
[12]	(a) Ding, R.; Sun, B.-F.; Lin, G.-Q. Org. Lett. 2012, 14, 4446. doi: 10.1021/ol301951r pmid: 24299147
	(b) Ding, R.; Fu, J.-G.; Xu, G.-Q.; Sun, B.-F.; Lin, G.-Q. J. Org. Chem. 2014, 79, 240. doi: 10.1021/jo402419h pmid: 24299147
	(c) Fu, J.-G.; Xu, G.-Q.; Ding, R.; Lin, G.-Q.; Sun, B.-F. Org. Chem. Front. 2016, 3, 62. doi: 10.1039/C5QO00355E pmid: 24299147
[13]	Haley, H. M. S.; Payer, S. E.; Papiddocha, S. M.; Clemens, S.; Nyenhuis, J.; Sarpong, R. J. Am. Chem. Soc. 2021, 143, 4732. doi: 10.1021/jacs.1c00457
[14]	(a) Xie, J.-H.; Zhou, Q.-L. Aldrichim. Acta 2015, 48, 33.
	(b) Lin, H.; Xiao, L.-J.; Zhou, M.-J.; Yu, H.-M.; Xie, J.-H.; Zhou, Q.-L. Org. Lett. 2016, 18, 1434. doi: 10.1021/acs.orglett.6b00369
	(c) Liu, Y.; Cheng, L.-J.; Yue, H.-T.; Che, W.; Xie, J.-H.; Zhou, Q.-L. Chem. Sci. 2016, 6, 4725.
	(d) Zou, X.-D.; Gou, S.-M.; Yang, R.; Xie, J.-H.; Zhou, Q.-L. Chem. Sci. 2017, 8, 6202. doi: 10.1039/C7SC02112G
	(e) Liu, Y.-T.; Li, L.-P.; Xie, J.-H.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2017, 56, 12708. doi: 10.1002/anie.v56.41
	(f) Zou, X.-D.; Gou, S.-M.; Yang, R.; Xie, J.-H.; Zhou, Q.-L. Org. Lett. 2017, 19, 5240. doi: 10.1021/acs.orglett.7b02517
	(g) Yang, X.-H.; Gu, X.-S.; Bin, H.-Y; Xie, J.-H.; Zhou, Q.-L. Chin. J. Org. Chem. 2020, 40, 3963. (in Chinese) doi: 10.6023/cjoc202007052
	(杨小会, 顾雪松, 宾怀玉, 谢建华, 周其林, 有机化学, 2020, 40, 3963.) doi: 10.6023/cjoc202007052
[15]	(a) Bin, H.-Y.; Wang, K.; Yang, D.; Yang, X.-H.; Xie, J.-H.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2019, 58, 1174. doi: 10.1002/anie.v58.4
	(b) Bin, H.-Y.; Cheng, L.; Wu, X.; Zhu, C.-L.; Yang, X.-H.; Xie, J.-H.; Zhou, Q.-L. Chem. Sci. 2021, 12, 7793. doi: 10.1039/D1SC02044G
[16]	(a) Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sinica 2014, 72, 778. (in Chinese) doi: 10.6023/A14050364
	(谢建华, 周其林, 化学学报, 2014, 72, 778.) doi: 10.6023/A14050364
	(b) Yang, X.-H.; Xie, J.-H.; Zhou, Q.-L. Org. Chem. Front. 2014, 1, 190. doi: 10.1039/c3qo00056g
	(c) Xie, J.-H.; Liu, X.-Y.; Xie, J.-B.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., nt. Ed. 2011, 50, 7329.
[17]	(a) Lu, S.-M.; Bolm, C. Angew. Chem.,Int. Ed. 2008, 47, 8920. doi: 10.1002/anie.v47:46
	(b) Lu, W.-J.; Chen, Y.-W.; Hou, X.-L. Angew. Chem.,Int. Ed. 2008, 47, 10133. doi: 10.1002/anie.v47:52
	(c) Tian, F.; Yao, D.; Liu, Y.; Xie, F.; Zhang, W. Adv. Synth. Catal. 2010, 352, 1841. doi: 10.1002/adsc.v352:11/12
	(d) Liu, X.; Han, Z.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2014, 53, 1978.

石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的不对称构建

Enantioselective Construction of the Pyridine-Fused Chiral Bicyclo- [3.3.1]nonane Skeleton of Huperzine A and Its Analogues

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 17

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951.
[2]	Jun Lu, Qichuang Li, Renxiao Liang, Yixia Jia. Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1875-1882.
[3]	Dongping Chen, Chunhong Yang, Ming Li, Guoxiao Zhao, Wenpeng Wang, Xicun Wang, Zhengjun Quan. Recent Progress on Arylation with Aryne through Three-Component Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 503-525.
[4]	Meijiao Sun, Jing Tan, Yu Tan, Jinsong Peng, Chunxia Chen. Pd-Catalyzed C(2)—H Arylation of 3-(2-Aminopyrimidin-4-yl)indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3945-3959.
[5]	Wei-Yuan Ma, Huifang Dai, Shaolin Kang, Tianlin Zhang, Xing-Zhong Shu. Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3614-3622.
[6]	Xuefeng Jia, Xiangjuan Tong. Recent Progress on Chan-Lam Coupling Reactions Catalyzed by Copper(II) Complexes [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2640-2658.
[7]	Xue Li, Cong Wang, Tiezheng Jia. Recent Advances in N-Arylation of NH-Sulfoximines and Their Applications [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 714-731.
[8]	Gaoxu Han, Hongtao Xu, Wei Hou. Rhodium(III) Catalyzed C(sp³)—H Functionalization [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 391-423.
[9]	Yamin Sun, Xiyong Li, Jinwei Yuan, Jialin Yu, Shuainan Liu. CuI-Catalyzed Regioselective Synthesis of 3-Arylcoumarins with Arylamines under Mild Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 631-640.
[10]	Xianghui Meng, Liangru Yang, Qilin Liu, Zhenhua Dong, Jinwei Yuan, Yongmei Xiao, Pu Mao. Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3747-3756.
[11]	Chenguang Liu, Qiang Liu. Earth-Abundant Metal-Catalyzed Asymmetric Hydrogenation of Carbon-Nitrogen Unsaturated Bonds [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3213-3220.
[12]	Yuxuan Zhang, Limin Xu, Yan Lu, Zhaoguo Zhang. Progress in Asymmetric Catalytic Reduction of Diketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3221-3239.
[13]	Fang Zhao, Wenjing Ye, Kai Wang. Advancement of Chiral Monodentate Phosphite Ligands in Asymmetric Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2650-2665.
[14]	Li Sheng, Haoling Gao, Xufeng Wu, Gang Fan, Pengcheng Liu. Rhodium/(2S,2'S,3S,3'S)-3,3'-Di-tert-butyl-4,4'-dimethoxy-2,2',3,3'-tetrahydro-2,2'-bibenzo[d][1,3]oxaphosphole (MeO-BIBOP) Catalyzed Synthesis of (R)-3-tert-Butoxy-carbonylamino-4-(2,4,5-trifluorophenyl)butyric Acid by Asymmetric Reduction of Enamines [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2105-2111.
[15]	Jun Zhang, Yafei Liu, Yurong Zhang, Liang Hu, Shiqing Han. Progress in Synthesis of 2-Substituted Benzothiazole Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1053-1071.