Organic Letters
Letter
1
physical data ([α]D, H and 13C NMR, IR, and HRMS) were
Hattori, F.; Suzuki, K. Chem. Commun. 2012, 48, 8425−8427.
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identical to those reported in literature.18
In summary, an efficient total synthesis of bis-C-glucosyl
flavonoid vicenin-2 (1) has been achieved via bis-β-C-
glucosylation of 1,3,5-trifluorobenzene and the transformation
of all fluorine atoms to oxygen functions. This method paves
the way to other bis-C-glycosyl natural products.
(7) For the preparation of lactone 4, see: Kuzuhara, H.; Fletcher, H.
G., Jr. J. Org. Chem. 1967, 32, 2531−2534.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
Full experimental procedures, characterization data, and
NMR spectra for all new compounds (PDF)
(11) For an example, see: Lee, D. Y. W.; Zhang, W.-Y.; Karnati, V. V.
R. Tetrahedron Lett. 2003, 44, 6857−6859.
AUTHOR INFORMATION
Corresponding Authors
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(12) For a review, see: (a) Amii, H.; Uneyama, K. Chem. Rev. 2009,
109, 2119−2183. For leading examples, see: (b) Rodriguez, J. R.;
Agejas, J.; Bueno, A. B. Tetrahedron Lett. 2006, 47, 5661−5663.
(c) Levin, J. I.; Du, M. T. Synth. Commun. 2002, 32, 1401−1406.
(d) Cantrell, W. R., Jr; Bauta, W. E.; Engles, T. Tetrahedron Lett. 2006,
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43, 3585−3587. (f) Krapcho, A. P.; Waterhouse, D. Synth. Commun.
1998, 28, 3415−3422. (g) Li, J.; Smith, D.; Qiao, J. X.; Huang, S.;
Krishnananthan, S.; Wong, H. S.; Salvati, M. E.; Balasubramanian, B.
N.; Chen, B.-C. Synlett 2009, 633−637. (h) Tsuji, H.; Cantagrel, G.;
Ueda, Y.; Chen, T.; Wan, L.-J.; Nakamura, E. Chem. - Asian J. 2013, 8,
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Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
This work was supported by JSPS KAKENHI Grants
JP23000006, JP16H06351, JP16H01137, and JP16H04107.
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(13) For an example, see: (a) Fujimoto, Y.; Watabe, Y.; Yanai, H.;
Taguchi, T.; Matsumoto, T. Synlett 2016, 27, 848−853. For the
mechanism, see: (b) Knudsen, R. D.; Snyder, H. R. J. Org. Chem. 1974,
39, 3343−3346. For the preparation of benzaldoxime, see:
(c) Tamilselvan, P.; Basavaraju, Y. B.; Sampathkumar, E.;
Murugesan, R. Catal. Commun. 2009, 10, 716−719.
(14) (a) Notes: using a stoichiometric amount of iodine in pyridine
afforded 11 in ca. 60% yield. For the original research paper on the use
of a catalytic amount of iodine, see: (b) Patonay, T.; Cavaleiro, J. A. S.;
Levai, A.; Silva, A. M. S. Heterocycl. Commun. 1997, 3, 223−229. For
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