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Copyright (c) 2014 Xianyou Wang1, Dongjun Gong1, Zhaohai Qin2
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Key Intermediate of Rocaglamide via SmI2 Catalyzed Intramolecular Reductive Coupling Reaction
Corresponding Author(s) : Xianyou Wang1
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
The compound of methyl 8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-2,3,3a,8a-tetrahydrocyclopenta[b]-benzofuran-2-carboxylate (3b), can be obtained with moderate yields under optimum reaction conditions. During this optimization, intramolecular ketone-ester reductive coupling reactions promoted by SmI2 have been studied. The synthetic procedure was successfully applied to the preparation of the key intermediate of the rocaglamide.
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References
O.N. Burchak and S. Py, Tetrahedron, 65, 7333 (2009).
P. Girard, J.L. Namy and H.B. Kagan, J. Am. Chem. Soc., 102, 2693 (1980).
(a) G.A. Molander, Chem. Rev., 92, 29 (1992); (b) G.A. Molander and C.R. Harris, Chem. Rev., 96, 307 (1996).
(a) A. Krief and A.M. Laval, Chem. Rev., 99, 745 (1999); (b) D.J. Edmonds, D. Johnston and D.J. Procter, Chem. Rev., 104, 3371 (2004).
J.E. McMurry and D.D. Miller, J. Am. Chem. Soc., 105, 1660 (1983).
Y.K. Liu and Y.M. Zhang, Tetrahedron Lett., 42, 5745 (2001).
M. Lu King, C.-C. Chiang, H.-C. Ling, E. Fujita, M. Ochiai and A.T. McPhail, J. Chem. Soc. Chem. Commun., 1150 (1982).
H.S. Li, B. Fu, N. Li, Y.-H. Dong and Z.H. Qin, Chin. J. Org. Chem., 25, 141 (2005).
A. Bermejo, J.R. Tormo, N. Cabedo, E. Estornell, B. Figadère and D. Cortes, J. Med. Chem., 41, 5158 (1998).
X.Y. Wang, N. Li, Y.Q. Ma and Zh.H. Qin, Acta Crystallogr., 65E, o2893 (2009).
T. Tsuritani, S. Ito, H. Shinokubo and K. Oshima, J. Org. Chem., 65, 5066 (2000).
F.R. Askham and K.M. Carroll, J. Org. Chem., 58, 7328 (1993).