Organic Letters
Letter
(24) (a) Hall, D. G.; Tailor, J.; Gravel, M. Angew. Chem., Int. Ed.
Notes
1999, 38, 3064. (b) Gravel, M.; Thompson, K. A.; Zak, M.; Ber
́ ́
ube, C.;
The authors declare no competing financial interest.
Hall, D. G. J. Org. Chem. 2002, 67, 3.
(25) Elgendy, S.; Patel, G.; Green, D.; Goodwin, C. A.; Scully, M. F.;
Husman, W.; Skordalakes, E.; Kakkar, V. V.; Deadman, J. J.
Tetrahedron Lett. 1997, 38, 3305.
(26) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527.
(27) Dunsdon, R. M.; Greening, J. R.; Jones, P. S.; Jordan, S.; Wilson,
F. X. Bioorg. Med. Chem. Lett. 2000, 10, 1577.
(28) (a) Hodge, P.; Waterhouse, J. J. Chem. Soc., Perkin Trans. 1
1983, 2319. (b) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546.
́ ́
(c) Maltais, R.; Berube, M.; Marion, O.; Labrecque, R.; Poirier, D.
Tetrahedron Lett. 2000, 41, 1691. (d) Maltais, R.; Luu-The, V.; Poirier,
D. Bioorg. Med. Chem. 2001, 9, 3101.
(29) Blaney, P.; Grigg, R.; Sridharan, V. Chem. Rev. 2002, 102, 2607.
(30) Sasubilli, R.; Gutheil, W. G. J. Comb. Chem. 2004, 6, 911.
(31) Castro, A. C.; Evans, C. A.; Grenier, L.; Grogan, M. J.
WO2010118159A1, Oct 14, 2010.
(32) Shreder, K. R.; Wong, M. S.; Corral, S.; Yu, Z.; Winn, D. T.; Wu,
M.; Hu, Y.; Nomanbhoy, T.; Alemayehu, S.; Fuller, S. R.; Rosenblum,
J. S.; Kozarich, J. W. Bioorg. Med. Chem. Lett. 2005, 15, 4256.
(33) (a) Springsteen, G.; Wang, B. Tetrahedron 2002, 58, 5291.
(b) Marinaro, W. A.; Prankerd, R.; Kinnari, K.; Stella, V. J. J. Pharm.
Sci. 2015, 104, 1399.
(34) Behnam, M. A. M.; Graf, D.; Bartenschlager, R.; Zlotos, D. P.;
Klein, C. D. J. Med. Chem. 2015, 58, 9354.
(35) Zinieris, N.; Leondiadis, L.; Ferderigos, N. J. Comb. Chem. 2005,
7, 4.
(36) Cudic, P.; Stawikowski, M. In Peptide-Based Drug Design; Otvos,
L., Ed.; Humana Press: 2008; Vol. 494, p 223.
ACKNOWLEDGMENTS
■
We thank Heiko Rudy and Tobias Timmermann for measuring
mass and NMR spectra and Dr. Veaceslav Boldescu for useful
discussions (all at IPMB). Mira Behnam appreciates financial
support from the German Academic Exchange Service. The
project was sponsored by the Deutsche Forschungsgemein-
schaft, KL-1356/3-1.
REFERENCES
■
(1) (a) Smoum, R.; Rubinstein, A.; Dembitsky, V. M.; Srebnik, M.
Chem. Rev. 2012, 112, 4156. (b) Soriano-Ursua, M. A.; Das, B. C.;
́
Trujillo-Ferrara, J. G. Expert Opin. Ther. Pat. 2014, 24, 485.
(2) Paramore, A.; Frantz, S. Nat. Rev. Drug Discovery 2003, 2, 611.
(3) Milani, P.; Demasi, M.; de Rezende, L.; Amaral, A. T. d.;
Andrade, L. H. New J. Chem. 2014, 38, 4859.
(4) Bull, S. D.; Davidson, M. G.; van den Elsen, J. M. H.; Fossey, J. S.;
Jenkins, A. T. A.; Jiang, Y.-B.; Kubo, Y.; Marken, F.; Sakurai, K.; Zhao,
J.; James, T. D. Acc. Chem. Res. 2013, 46, 312.
(5) Chen, M.-L.; Adak, A. K.; Yeh, N.-C.; Yang, W.-B.; Chuang, Y.-J.;
Wong, C.-H.; Hwang, K.-C.; Hwu, J.-R. R.; Hsieh, S.-L.; Lin, C.-C.
Angew. Chem., Int. Ed. 2008, 47, 8627.
(6) Huang, L.-D.; Adak, A. K.; Yu, C.-C.; Hsiao, W.-C.; Lin, H.-J.;
Chen, M.-L.; Lin, C.-C. Chem. - Eur. J. 2015, 21, 3956.
(7) Hoffmann, R.; Hummel, H.; Weiler, V. US20100041162A1, Feb
18, 2010.
(37) Hall, D. G. Boronic Acids; Wiley-VCH Verlag GmbH & Co.
KGaA: 2006; p 1.
(38) (a) Bastos Lima, A.; Behnam, M. A. M.; El Sherif, Y.; Nitsche,
C.; Vechi, S. M.; Klein, C. D. Bioorg. Med. Chem. 2015, 23, 5748.
(b) Weigel, L. F.; Nitsche, C.; Graf, D.; Bartenschlager, R.; Klein, C. D.
J. Med. Chem. 2015, 58, 7719.
(8) Stolowitz, M. L.; Ahlem, C.; Hughes, K. A.; Kaiser, R. J.; Kesicki,
E. A.; Li, G.; Lund, K. P.; Torkelson, S. M.; Wiley, J. P. Bioconjugate
Chem. 2001, 12, 229.
(9) Ueno, H.; Iwata, T.; Koshiba, N.; Takahashi, D.; Toshima, K.
Chem. Commun. 2013, 49, 10403.
(10) Kanekiyo, Y.; Naganawa, R.; Tao, H. Chem. Commun. 2004,
1006.
(11) Zhang, L.; Cheng, Y.; Lei, J.; Liu, Y.; Hao, Q.; Ju, H. Anal. Chem.
2013, 85, 8001.
(12) Yang, Y.-L.; Lee, Y.-P.; Yang, Y.-L.; Lin, P.-C. ACS Chem. Biol.
2014, 9, 390.
(13) Miyahara, T.; Kurihara, K. J. Am. Chem. Soc. 2004, 126, 5684.
(14) (a) Huang, Y.-J.; Ouyang, W.-J.; Wu, X.; Li, Z.; Fossey, J. S.;
James, T. D.; Jiang, Y.-B. J. Am. Chem. Soc. 2013, 135, 1700.
(b) Bellott, E. M.; Bu, D.; Childs, J. J.; Lambert, C.; Nienaber, H. A.;
Shi, S. J.; Wang, Z.; Workman, J. J.; Zelenchuk, A. R. US8029765B2,
Oct 4, 2011.
(15) (a) Westmark, P. R.; Gardiner, S. J.; Smith, B. D. J. Am. Chem.
Soc. 1996, 118, 11093. (b) Morin, G. T.; Hughes, M. P.; Paugam, M.-
F.; Smith, B. D. J. Am. Chem. Soc. 1994, 116, 8895.
(16) Matsumoto, A.; Kataoka, K.; Miyahara, Y. Polym. J. 2014, 46,
483.
(17) (a) Kashiwada, A.; Tsuboi, M.; Matsuda, K. Chem. Commun.
2009, 695. (b) Analoui, M.; Annapragada, A.; Dasgupta, I.; Srivastava,
M.; Tanifum, E. WO2012119117A1, Sep 7, 2012.
(18) Takahashi, D.; Miura, T.; Toshima, K. Chem. Commun. 2012,
48, 7595.
(19) Xu, L.; Hu, Y.; Liu, M.; Chen, J.; Huang, X.; Gao, W.; Wu, H.
Tetrahedron 2015, 71, 2079.
(20) Zhang, W.; Bryson, D. I.; Crumpton, J. B.; Wynn, J.; Santos, W.
L. Chem. Commun. 2013, 49, 2436.
(21) (a) Hodge, P. Chem. Soc. Rev. 1997, 26, 417. (b) Hodge, P. Ind.
Eng. Chem. Res. 2005, 44, 8542. (c) Guillier, F.; Orain, D.; Bradley, M.
Chem. Rev. 2000, 100, 2091.
(22) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
(23) (a) Carboni, B.; Pourbaix, C.; Carreaux, F.; Deleuze, H.;
Maillard, B. Tetrahedron Lett. 1999, 40, 7979. (b) Pourbaix, C.;
Carreaux, F.; Carboni, B.; Deleuze, H. Chem. Commun. 2000, 1275.
D
Org. Lett. XXXX, XXX, XXX−XXX