Concise syntheses of 13-methylprotoberberine and 13-methyltetrahydroprotoberberine alkaloids
-
* Corresponding authors.
E-mail addresses: peitang@scu.edu.cn (P. Tang), rfchen@fudan.edu.cn (F. Chen).
Citation: Wenchang Chen, Xiaofen Yi, Hongmin Qu, Yu Chen, Pei Tang, Fener Chen. Concise syntheses of 13-methylprotoberberine and 13-methyltetrahydroprotoberberine alkaloids[J]. Chinese Chemical Letters, ;2022, 33(12): 5080-5083. doi: 10.1016/j.cclet.2022.04.047
L. Grycova, J. Dostal, R. Marek, Phytochemistry 68 (2007) 150–175.
doi: 10.1016/j.phytochem.2006.10.004
Z. Liu, Z. Mi, P. Wang, et al., Nat. Prod. Res. 34 (2020) 3305–3312.
doi: 10.1080/14786419.2019.1566821
K. Iwasa, C. Kim, Phytochemistry 46 (1997) 1359–1363.
doi: 10.1016/S0031-9422(97)00500-1
J.H. Kim, Y.B. Ryu, W.S. Lee, Y.H. Kim, Bioorg. Med. Chem. 22 (2014) 6047–6052.
doi: 10.1016/j.bmc.2014.09.004
J.W. Han, S.H. Shim, K.S. Jang, et al., J. Microbiol. Biotechnol. 28 (2018) 262–266.
doi: 10.4014/jmb.1707.07009
J. Zhou, G. Peng, J. Li, et al., Trop. J. Pharm. Res. 15 (2016) 141–148.
N. Bribi, F. Algieri, A.R. Nogales, et al., Phytomedicine 23 (2016) 901–913.
doi: 10.1016/j.phymed.2016.05.003
K.C. Chang, Y.S. Ko, H.J. Kim, D.Y. Nam, D.U. Lee, Int. Immunopharmacol. 40 (2016) 269–276.
doi: 10.1016/j.intimp.2016.08.022
Q. Huang, J. Bi, Q. Sun, et al., Planta. Med. 78 (2012) 65–70.
doi: 10.1055/s-0031-1280126
J. Chlebek, J. Korabecny, R. Dolezal, et al., Molecules 24 (2019) 1340–1350.
doi: 10.3390/molecules24071340
H. Li, T. Han, R. Liu, et al., Chem. Biodivers. 5 (2008) 777–783.
doi: 10.1002/cbdv.200890074
K. Iwasa, Y. Nishiyama, M. Ichimaru, et al., Eur. J. Med. Chem. 34 (1999) 1077–1083.
doi: 10.1016/S0223-5234(99)00127-0
C. Gupta, M. Khan, M. Khan, A.K. Tiwari, Interdiscip. Sci. Comput. Life. Sci. 5 (2013) 136–144.
doi: 10.1007/s12539-013-0164-y
Y. Chow, M. Sogame, F. Sato, Sci. Rep. 6 (2016) 38129–38138.
doi: 10.1038/srep38129
Z. Peng, H. Zhan, Y. Shao, et al., Chin. Med. 15 (2020) 8–19.
doi: 10.1186/s13020-020-0286-1
K. Iwasa, M. Kamigauchil, M. Uek, M. Taniguch, Eur. J. Med. Chem. 31 (1996) 469–478.
doi: 10.1016/0223-5234(96)85167-1
M. Cushman, J. Gentry, F.W. Dekow, J. Org. Chem. 42 (1977) 1111–1116.
doi: 10.1021/jo00427a001
C. Kitsiou, W.P. Unsworth, G. Coulthard, R.J.K. Taylor, Tetrahedron 70 (2014) 7172–7180.
doi: 10.1016/j.tet.2014.04.066
L. Ma, D. Seidel, Chem. Eur. J. 21 (2015) 12908–12913.
doi: 10.1002/chem.201501667
J. Jayakumar, C. Cheng, Chem. Eur. J. 22 (2016) 1800–1804.
doi: 10.1002/chem.201504378
A.E. Gatland, B.S. Pilgrim, P.A. Procopiou, T.J. Donohoe, Angew. Chem. Int. Ed. 53 (2014) 14555–14558.
doi: 10.1002/anie.201409164
S. Zhou, R. Tong, Chem. Eur. J. 22 (2016) 7084–7089.
doi: 10.1002/chem.201601245
S. Zhou, R. Tong, Org. Lett. 19 (2017) 1594–1597.
doi: 10.1021/acs.orglett.7b00414
L. Mengozzi, A. Gualandi, P.G. Cozzi, Chem. Sci. 5 (2014) 3915–3921.
doi: 10.1039/C4SC01221F
R. Roddan, F. Subrizi, J. Broomfield, et al., Org. Lett. 23 (2021) 6342–6347.
doi: 10.1021/acs.orglett.1c02110
L.M. Quiroz, S.L. Hedrick, A.R. Santos, M.D. Clift, Org. Lett. 20 (2018) 4281–4284.
doi: 10.1021/acs.orglett.8b01702
P. Yang, D. Song, Y. Li, et al., Bioorg. Med. Chem. Lett. 18 (2008) 4675–4677.
doi: 10.1016/j.bmcl.2008.07.005
P. Tang, H. Wang, W. Zhang, F. Chen, Green Synth. Catal. 1 (2020) 26–41.
doi: 10.1016/j.gresc.2020.05.006
W. Li, M. Jiang, W. Chen, et al., J. Org. Chem. 86 (2021) 8143–8153.
doi: 10.1021/acs.joc.1c00602
W. Zhang, X. Chen, Y. An, et al., Chem. Eur. J. 26 (2020) 10439–10443.
doi: 10.1002/chem.202002404
E.R. Welin, A. Ngamnithiporn, M. Klatte, et al., Science 363 (2019) 270–275.
doi: 10.1126/science.aav3421
T. Morimoto, N. Suzuki, K. Achiwa, Tetrahedron: Asymmetry 9 (1998) 183–187.
doi: 10.1016/S0957-4166(97)00635-6
L. Shi, Z.S. Ye, L.L. Cao, et al., Angew. Chem. Int. Ed. 51 (2012) 8286–8289.
doi: 10.1002/anie.201203647
Yue Li , Minghao Fan , Conghui Wang , Yanxun Li , Xiang Yu , Jun Ding , Lei Yan , Lele Qiu , Yongcai Zhang , Longlu Wang . 3D layer-by-layer amorphous MoSx assembled from [Mo3S13]2- clusters for efficient removal of tetracycline: Synergy of adsorption and photo-assisted PMS activation. Chinese Chemical Letters, 2024, 35(9): 109764-. doi: 10.1016/j.cclet.2024.109764
Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H2O2 in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926
Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO2 adsorption and conversion: Modification methods, reaction condition, and CO2 hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
Xinxiu Yan , Xizhe Huang , Yangyang Liu , Weishang Jia , Hualin Chen , Qi Yao , Tao Chen . Hyperbranched polyamidoamine protective layer with phosphate and carboxyl groups for dendrite-free Zn metal anodes. Chinese Chemical Letters, 2024, 35(10): 109426-. doi: 10.1016/j.cclet.2023.109426
Yunfei Shen , Long Chen . Gradient imprinted Zn metal anodes assist dendrites-free at high current density/capacity. Chinese Journal of Structural Chemistry, 2024, 43(10): 100321-100321. doi: 10.1016/j.cjsc.2024.100321
Shuo Zhang , Haitao Liao , Zhi-Qun Liu , Chong Yan , Jia-Qi Huang . Re-evaluating the nano-sized inorganic protective layer on Cu current collector for anode free lithium metal batteries. Chinese Chemical Letters, 2024, 35(7): 109284-. doi: 10.1016/j.cclet.2023.109284