Research on the Semi-synthesis of Pectolinarin from Scutellarin
- Corresponding author: Li Yingxia, liyx417@fudan.edu.cn
Citation:
Yan Shiqiang, Xie Mingxian, Wang Yujie, Li Yingxia. Research on the Semi-synthesis of Pectolinarin from Scutellarin[J]. Chinese Journal of Organic Chemistry,
;2019, 39(2): 412-418.
doi:
10.6023/cjoc201807051
Morimoto, M.; Tanimoto, K.; Nakano, S.; Ozaki, T.; Nakano, A.; Komai, K. J. Agric. Food Chem. 2003, 51, 389.
doi: 10.1021/jf025627a
Bandele, O. J.; Osheroff, N. Biochemistry 2007, 46, 6097.
doi: 10.1021/bi7000664
Daskiewicz, J. B.; Depeint, F.; Viornery, L.; Bayet, C.; Comte-Sarrazin, G.; Comte, G.; Gee, J. M.; Johnson, I. T.; Ndjoko, K. K.; Hostettmann, K.; Barron, D. J. Med. Chem. 2005, 48, 2790.
doi: 10.1021/jm040770b
Meragelman, T. L.; Tucker, K. D.; McClord, T. G.; Cardel-lina, J. H.; Shoemker, R. H. J. Nat. Prod. 2005, 68, 1790.
doi: 10.1021/np0503000
Na, M.; Jang, J.; Njamen, D.; Mbafor, J. T.; Fomum, Z. T.; Kim, B. Y.; Oh, W. K.; Ahn, J. S. J. Nat. Prod. 2006, 69, 1572.
doi: 10.1021/np0601861
Prestos, C.; Boziaris, I. S.; Nychas, J. E. Food Chem. 2005, 93, 1998.
Yoon, H.; Kim, T. W.; Shin, S. Y.; Park, M. J.; Yong, Y.; Kim, D. W.; Islam, T.; Lee, Y. H.; Jung, K. Y.; Lim, Y. Biol. Med. Chem. Lett. 2013, 23, 232.
doi: 10.1016/j.bmcl.2012.10.130
Rahman, M. M.; Gray, A. I.; Khondkar, P.; Sarker, S. D. Pharm. Biol. 2008, 46, 356.
Hirpara, K. V.; Aggarwal, A. J.; Mukherjee, N.; Joshi; Burman, A. C. Curr. Med. Chem. 2009, 9, 138.
Nawghare, B.; Funde, S.; Raheem, A.; Lokhande, P. Chin. J. Chem. 2012, 30, 1695.
doi: 10.1002/cjoc.v30.8
Walle, T.; Vincent, T. S.; Walle, U. K. Biochem. Pharmacol. 2003, 65, 1603.
doi: 10.1016/S0006-2952(03)00151-5
Tang, L.-J.; Zang, S.-F.; Yang, J.-Z.; Gao, W.-T. Chin. J. Org. Chem. 2004, 24, 882(in Chinese).
doi: 10.3321/j.issn:0253-2786.2004.08.005
Ishida, H.; Umino, T.; Tsuji, K.; Kosuge, T. Chem. Pharm. Bull. 1987, 35, 861.
doi: 10.1248/cpb.35.861
(a) Park, J. C.; Lee, J. H.; Choi, J. S. Phytochemistry 1995, 39, 261.
(b) Lim, H.; Son, K. H.; Chang, H. W.; Bae, K.; Kang, S. S.; Kim, H. P. Biol. Pharm. Bull. 2008, 31, 2063.
Liu, S. J.; Luo, X.; Li, D. X.; Zhang, J.; Qiu, D. L.; Liu, W.; She, L.; Yang, Z. R. Int. Immunopharmacol. 2006, 6, 1387.
doi: 10.1016/j.intimp.2006.02.002
Yoo, Y. M.; Nam, J. H.; Kim, M. Y.; Choi, J.; Park, H. J. Biol. Pharm. Bull. 2008, 31, 760.
doi: 10.1248/bpb.31.760
Lee, S.; Lee, D. H.; Kim, J. C.; Um, B. H.; Sung, S. H.; Jeong, L. S.; Kim, Y. K.; Kim, S. N. Biochem. Biophys. Res. Commun. 2017, 493, 765.
doi: 10.1016/j.bbrc.2017.08.106
Thamere, C.; Mourad, H.; Amel, B.; Nadir, B.; Ines, M.; Ramdane, S.; Souad, A.; Ahmed, M.; Fadila, B.; Samir, B. Nat. Prod. Res. 2017, 31, 2042.
doi: 10.1080/14786419.2016.1274889
Tundis, R.; Deguin, B.; Loizzo, M. R.; Bonesi, M.; Statti, G. A.; Tillequin, F.; Menichini, F. Bioorg. Med. Chem. Lett. 2005, 15, 4757.
doi: 10.1016/j.bmcl.2005.07.029
Chen, Z.-W.; Hu, J.-Z. Chin. J. Org. Chem. 2006, 26, 813(in Chinese).
doi: 10.3321/j.issn:0253-2786.2006.06.008
Quintin, J.; Lewin, G. J. Nat. Prod. 2004, 67, 1624.
doi: 10.1021/np040079b
Jiang, X. Y.; Li, X. C.; Liu, W. Y.; Xu, Y. H.; Feng, F.; Qu, W. Tetrahedron 2017, 73, 1895.
doi: 10.1016/j.tet.2017.02.039
Yan, S. Q.; Ding, N.; Zhang, W.; Wang, P.; Li, Y. X.; Li, M. Carbohydr. Res. 2012, 354, 6.
doi: 10.1016/j.carres.2012.02.021
Zhang, M.; Du, Y.; Kong, F. Carbohydr. Res. 2001, 330, 319.
doi: 10.1016/S0008-6215(00)00303-7
Kang, M. M.; Ma, Z. L.; Liu, B.; Pan, D.; Li, J. Q. Chin. J. Org. Chem. 2017, 37, 1516(in Chinese).
Maharik, N. A.; Botting, N. P. Eur. J. Org Chem. 2008, 5622.
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Reagents and conditions: (a) SOCl2 (10.0 equiv.), MeOH, 93%; (b) MeI (2.4 equiv.), K2CO3 (3.0 equiv.), DMF, 84%; (c) H2SO4, EtOH, reflux, 89%
Reagents and conditions: (a) TBDPSCl (1.5 equiv.), Im (3.0 equiv.), BzCl (6.0 equiv.), Py, 73%; (b) TfOH-SiO2 (0.2 equiv.), MeCN, 89%; (c) 12 (1.2 equiv.), TMSOTf (0.15 equiv.), 67%; (d) AcBr (5.0 equiv.), MeOH (3.0 equiv.), AcOH, 8 h, 88%
Reagents and conditions: (a) TBAB (0.5 equiv.), aq. K2CO3, 45 ℃, 18 h, 62%; (b) K2CO3 (2.0 equiv.), THF-MeOH-H2O, 2 h, 89%