Chinese Journal of Organic Chemistry >
Total Synthesis of Lycogarubin C and Lycogalic Acid A
Received date: 2014-03-11
Revised date: 2014-04-08
Online published: 2014-04-16
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21072083, 21272104), the Research Fund for the Doctoral Program of Higher Education of China (No. 20110211110009) and the Fundamental Research Funds for the Central Universities (No. lzujbky-2012-56).
Lycogarubin C and lycogalic acid A are key marine natural products which are used in studies on inhibitor of DNA Topoisomerase-I. With (but-3-ynyloxy)(tert-butyl)dimethylsilane as starting material, lycogarubin C was prepared in the process with 8 steps, via hetero-/retro-Diels-Alder reaction, reduction of 1,2-diazine, Swern oxidation, and Fischer indole synthesis as the key reactions, and lycogalic acid A was also obtained in the reaction of lycogarubin C with potassium hydroxide.
Zhou Nini , Shi Qian , Xie Zhixiang . Total Synthesis of Lycogarubin C and Lycogalic Acid A[J]. Chinese Journal of Organic Chemistry, 2014 , 34(6) : 1104 -1109 . DOI: 10.6023/cjoc201403025
[1] Sanchez, C.; Mendez, C.; Salas, J. A. Nat. Prod. Rep. 2006, 23, 1007.
[2] Ryan, K. S.; Drennan, C. L. Chem. Biol. 2009, 16, 351.
[3] Zhang, W. J.; Liu, Z.; Li, S. M.; Yang, T. T.; Zhang, Q B.; Ma, L.; Tian, X. P.; Zhang, H. B.; Huang, C. G.; Zhang, S.; Ju, J. H.; Shen, Y. M.; Zhang, C. S. Org. Lett. 2012, 14, 3364.
[4] McArthur, K. A.; Mitchell, S. S.; Tsueng, G.; Rheingold, A.; White, D. J.; Grodberg, J.; Lam, K. S.; Potts, B. C. J. Nat. Prod. 2008, 71, 1732.
[5] (a) Frode, R.; Hinze, C.; Josten, I.; Schmidt, B.; Steffan, B.; Steglich, W. Tetrahedron Lett. 1994, 35, 1689.
(b) Hashimoto, T.; Yasuda, A.; Akazawa, K.; Takaoka, S.; Tori, M.; Akazawa, Y. Tetrahedron Lett. 1994, 35, 2559.
[6] Knolker, H-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
[7] Nishizawa, T.; Gruschow, S.; Jayamaha, D.-H. E.; Nishizawa-Haraha, C.; Sherman, D. H. J. Am. Chem. Soc. 2006, 128, 724.
[8] a) Fürstner, A.; Krause, H.; Thiel, O. R. Tetrahedron 2002, 58, 6373.
(b) Hinze, C.; Kreipl, A.; Terpin, A.; Steglich, W. Synthesis 2007, 4, 608.
(c) Fu, L. F.; Gribble, G. W. Tetrahedron Lett. 2010, 51, 537.
(d) Oakdale, J. S.; Boger, D. L. Org. Lett. 2010, 12, 1132.
(e) Chen, W.; Hao, H. L.; Zhang, C. L; Shen, Y. M. Chin. J. Org. Chem. 2014, 34, 797 (in Chinese).
(陈旺, 郝慧琳, 张晨露, 沈月毛, 有机化学, 2014, 34, 797.)
[9] Kawasaki, Y.; Ishikawa, Y.; Igawa, K.; Tomooka, K. J. Am. Chem. Soc. 2011, 133, 20712.
[10] Boger, D. L.; Coleman, R. S.; Panek, J. S.; Huber, F. X.; Sauer, J. J. Org. Chem. 1985, 50, 5377.
[11] Lionel, M.; Severin, O.; Naran G.; Alexandre, C.; Julius, R. J. Eur. J. Org. Chem. 2008. 20, 1673.
[12] Boger, D. L.; Soenen, D. R.; Boyce, C. W.; Hedrick, M. P.; Jin, Q. J. Org. Chem. 2000, 65, 2479.
[13] Eggen, M.; Nair, S. K; Georg, G. I. Org. Lett. 2001, 3, 1813.
[14] Hollinshead, D. M.; Howell, S. C.; Ley, S.V.; Mahon, M.; Ratcligffe, N. M.; Worthington, P. A. J. Chem. Soc., Perkin. Trans. 1 1983, 1579.
[15] Wang, J.-J.; Shim, Y.-K.; Jiang, G.-J.; Imafuku, K. J. Heterocycl. Chem. 2003, 40, 1075.
[16] Chaudhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 20, 99.
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