Chinese Journal of Organic Chemistry >
Total Synthesis of (±)-Galbulin and (±)-8,8'-Epi-aristoligone
Received date: 2016-06-11
Revised date: 2016-07-20
Online published: 2016-08-22
Supported by
Project supported by the Special Fund of the Applied Basic Research Plan of Yunnan Provincial Science and Technology Department-Kunming Medical University (No. 2014FB014).
(±)-Galbulin and (±)-8,8'-epi-aristoligone belong to cyclolignan family, and exhibit varieties of bioactivities. Using Horner-Wadsworth-Emmons and Friedel-Crafts reactions as key steps, galbulin has been successfully synthesized in eight steps from 3,4-dimethoxy-phenylacetic acid, and (±)-8,8'-epi-aristoligone was obtained by oxidation of (±)-galbulin. The method is simple and easy to operate, which provides a reference for the synthesis of cyclolignan compounds.
Key words： galbulin; aristoligone; total synthesis
Wang Kou , Qin Hongbo , Li Mingming . Total Synthesis of (±)-Galbulin and (±)-8,8'-Epi-aristoligone[J]. Chinese Journal of Organic Chemistry, 2016 , 36(12) : 2928 -2932 . DOI: 10.6023/cjoc201606016
[1] Ayres, D. C.; Loike, J. D. Lignans:Chemical, Biological and Clinical Properties, Cambridge University Press, New York, 1990.
[2] Kasatkin, A. N.; Checksfield, G.; Whitby, R. J. J. Org. Chem. 2000, 65, 3236.
[3] Datta, P. K.; Yau, C.; Hooper, T. S.; Yvon, B. L.; Charlton, J. L. J. Org. Chem. 2001, 66, 8606.
[4] Hong, B. C.; Hsu, C. S.; Lee, G. H. Chem. Commun. 2012, 48, 2385.
[5] Peng, Y.; Luo, Z. B.; Zhang, J. J.; Luo, L.; Wang, Y. W. Org. Biomol. Chem. 2013, 11, 7574.
[6] Li, X. Y.; Jiao, X. Z.; Liu, X. Y.; Tian, C. S.; Dong, L.; Yao, Y. Y.; Xie, P. Tetrahedron Lett. 2014, 55, 6324.
[7] Chen, W.-H; Wang, C.; Fan, L.-L.; Wang, J.-T.; Yue, W.-Z.; Tang, L. Chin. J. Org. Chem. 2015, 35, 1146(in Chinese).(陈文章, 王聪, 樊玲玲, 王建塔, 岳炜洲, 汤磊, 有机化学, 2015, 35, 1146.)
[8] Xiu, Z.-M.; Wang, L.-C.; Huang, M.-Y.; Zhang, P.; Guo, Y.-M.; Zhang, W.-Q.; Wang, L.-P. Chin. J. Org. Chem. 2014, 34, 1786(in Chinese).(修志明, 王立成, 黄梦媛, 张鹏, 郭佑铭, 张闻起, 王丽萍, 有机化学, 2014, 34, 1786.)
[9] Xu, Z.-H.; Pan, S.; Huang, Y.-G. Chin. J. Org. Chem. 2014, 34, 1391(in Chinese).(徐之涵, 潘燊, 黄焰根, 有机化学, 2014, 34, 1391.)
[10] Ghorai, M. K.; Kumar, A.; Tiwari, D. P. J. Org. Chem. 2010, 75, 137.
[11] Felluga, F.; Ghelfi, F.; Pitacco, G.; Roncaglia, F.; Valentin, E.; Venneri, C. D. Tetrahedron:Asymmetry 2010, 21, 2183.
[12] Denissova, I.; Maretti, L.; Wilkes, B. C.; Scaiano, J. C.; Guindon, Y. J. Org. Chem. 2009, 74, 2438.
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