DOI: 10.1039/C3CC45139A
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fused butenolides and their analogues, which are core skeletons
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17
of many natural substances
. To witness the synthetic
applications of our protocol, the reductive transformation of the
cyclization product 3e was conducted (Scheme 2), while
compound 3e was unexpectedly isomerized to the fused
butenolide 4 in the presence of Pd-C/H2 in THF at room
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5
55
temperature in 41% yield. Further experiment showed
CuCl/NaBH4 complex can successfully reduce 3e to the expected
fused dihydrofuran-2(3H)-one derivative in 38% yield
10 and >99:1 dr.
a
5
60 5 For selected examples: (a) X. Jiang, Y. Cao, Y. Wang, L. Liu, F. Shen,
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Scheme 2 Synthetic application of this approach
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Z. J. Wu, X. M. Zhang, W. C. Yuan, Org. Lett., 2012, 14, 490.
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In summary, we have firstly developed an organocatalytic
asymmetric allylic alkylation/cyclization of 3-hydroxyoxindoles
15 with MBH carbonates, which furnished highly functionalized
spirooxindoles bearing α-methylene-γ-butyrolactone motifs in
good yields and with excellent diastereo- and enantioselectivities.
This protocol also provided an effective method for the
construction of fused butenolides and their analogues. Further
20 studies to explore the reaction mechanism and extend its scope
are underway in our lab.
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Acknowledgement
We are grateful for the financial support from National Natural
Science Foundation of China (No. 21272230) and Western Light
25 Talent Culture Project.
80
11 S. Gemma, G. Campiani, S. Butini, B. P. Joshi and G. Kukreja, J. Med.
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Notes and references
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Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese
Academy of Sciences, Chengdu 610041, China;Email:wlxioc@cioc.ac.cn;
85
b
University of Chinese Academy of Sciences, Beijing 10049, China
† Electronic Supplementary Information (ESI) available: Experimental
procedures, spectral data of new compounds, and crystallographic data
See DOI: 10.1039/b000000x/
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