Organic Letters
Letter
(11) Sakurai, K.; Fukumoto, T.; Noguchi, K.; Sato, N.; Asaka, H.;
Moriyama, N.; Yohda, M. Org. Lett. 2010, 12, 5732−5735.
(12) (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643−663.
(b) Allen, C. L.; Miller, S. J. Org. Lett. 2013, 15, 6178−6181. (c) Helm,
R. F.; Ralph, J. J. Org. Chem. 1991, 56, 7015−7021. (d) Sun, X.; Lee,
H.; Lee, S.; Tan, K. L. Nat. Chem. 2013, 5, 790−795. (e) Lee, D.;
Taylor, M. S. J. Am. Chem. Soc. 2011, 133, 3724−3727. (f) Lee, D.;
Williamson, C. L.; Chan, L.; Taylor, M. S. J. Am. Chem. Soc. 2012, 134,
8260−8267. (g) Chen, I.-H.; Kou, K. G. M.; Le, D. N.; Rathbun, C.
M.; Don, V. M. Chem.Eur. J. 2014, 20, 5013−5018.
used to show its cell uptake and cellular localization. Efforts to
identify previously unknown OSW-1 binding proteins are
currently ongoing using the biotin-tagged OSW-1.
ASSOCIATED CONTENT
* Supporting Information
■
S
Experimental procedures, structural characterization data, and
fluorescence spectra. This material is available free of charge via
(13) Demizu, Y.; Kubo, Y.; Miyoshi, H.; Maki, T.; Matsumura, Y.;
Moriyama, N.; Onomura, O. Org. Lett. 2008, 10, 5075−5077.
(14) Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman,
L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210−
216.
AUTHOR INFORMATION
Corresponding Author
■
+81-42-388-7374.
(15) For the cellular uptake and localization of 3″-DBD-tagged
OSW-1 under the same experimental conditions as that for 5, see
Figure S3 (Supporting Information).
Author Contributions
‡T.T. and M.H. contributed equally.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was funded by a JSPS Grant-in-Aid for Challenging
Exploratory Research (No. 25560400). R.Y. is supported by a
Teijin−Kumura scholarship.
REFERENCES
■
(1) Kubo, S.; Mimaki, Y.; Terao, M.; Sashida, Y.; Nikaido, T.;
Ohmoto, T. Phytochemistry 1992, 31, 3969−3973.
(2) (a) Guo, C.; Fuchs, P. L. Tetrahedron Lett. 1998, 39, 1099−1102.
(b) Deng, S.; Yu, B.; Lou, Y.; Hui, Y. J. Org. Chem. 1999, 64, 202−208.
(c) Yu, W.; Jin, Z. J. Am. Chem. Soc. 2001, 123, 3369−3370. (d) Yu,
W.; Jin, Z. J. Am. Chem. Soc. 2002, 124, 6576−6583. (e) Morzycki, J.
W.; Wojtkielewicz, A. Carbohydr. Res. 2002, 337, 1269−1274. (f) Shi,
B.; Tang, P.; Hu, X.; Liu, J. O.; Yu, B. J. Org. Chem. 2005, 70, 10354−
10367. (g) Tsubuki, M.; Matsuo, S.; Honda, T. Tetrahedron Lett. 2008,
49, 229−232. (h) Xue, J.; Liu, P.; Pan, Y. B.; Guo, Z. W. J. Org. Chem.
2008, 73, 157−161.
(3) Mimaki, Y.; Kuroda, M.; Kameyama, A.; Sashida, Y.; Hirano, T.;
Oka, K.; Maekawa, R.; Wada, T.; Sugita, K.; Buetler, J. A. Bioorg. Med.
Chem. Lett. 1997, 7, 633−636.
(4) Kuroda, M.; Hasegawa, F.; Yokosuka, A.; Mimaki, Y.; Sashida, Y.
Meeting Abstract. Symp. Chem. Nat. Prod. 2001, 43, 371−376.
(5) Tang, Y.; Ji, N.; Duan, J.; Tao, W. Chem. Rev. 2013, 113, 5480−
5514.
(6) Burgett, W. G. A.; Poulsen, B. T.; Wangkanont, K.; Anderson, R.
D.; Kikuchi, C.; Shimada, K.; Okubo, S.; Fortner, C. K.; Mimaki, Y.;
Kuroda, M.; Murphy, P. J.; Schwalb, J. D.; Petrella, C. E.; Cornella-
Taracido, I.; Schirle, M.; Tallarico, A. J.; Shair, D. M. Nat. Chem. Biol.
2011, 7, 639−647.
(7) Garcia-Prieto, C.; Ahmed, K. B. R.; Chen, Z.; Hammoudi, N.;
Kang, Y.; Lou, C.; Mei, Y.; Jin, Z.; Huang, P. J. Biol. Chem. 2013, 288,
3240−3250.
(8) (a) Robles, O.; Romo, D. Nat. Prod. Rep. 2014, 31, 318−334.
(b) Bottcher, T.; Pitscheider, M.; Sieber, S. A. Angew. Chem., Int. Ed.
̈
2010, 49, 2680−2698. (c) Leslie, B. J.; Hergenrother, P. J. Chem. Soc.
Rev. 2008, 37, 1347−1360. (d) Carlson, E. E. ACS Chem. Biol. 2010, 5,
639−653.
(9) Yamada, R.; Takeshita, T.; Hiraizumi, M.; Shinohe, D.; Ohta, Y.;
Sakurai, K. Bioorg. Med. Chem. Lett. 2014, 24, 1839−1842.
(10) (a) Kurahashi, T.; Mizutani, T.; Yoshida, J. Tetrahedron 2002,
58, 8669−8677. (b) Lewis, C. A.; Miller, S. J. Angew. Chem., Int. Ed.
2006, 45, 5616−5619. (c) Wilcock, B. C.; Uno, B. E.; Bromann, G. L.;
Clark, M. J.; Anderson, T. M.; Burke, M. E. Nat. Chem. 2012, 4, 996−
1003. (d) Ueda, Y.; Mishiro, K.; Yoshida, K.; Furuta, T.; Kawabata, T.
J. Org. Chem. 2012, 77, 7850−7857.
D
dx.doi.org/10.1021/ol503044j | Org. Lett. XXXX, XXX, XXX−XXX