E
T.-K. Chui, H.-F. Chow
Letter
Synlett
Funding Information
(15) (a) Li, Y.; Flood, A. H. Angew. Chem. Int. Ed. 2008, 47, 2649.
(b) Hua, Y.; Flood, A. H. Chem. Soc. Rev. 2010, 39, 1262. (c) Yim,
S.-L.; Chow, H.-F.; Chan, M.-C. Chem. Commun. 2014, 50, 3064.
(d) Flood, A. H. Beilstein J. Org. Chem. 2016, 12, 611.
(16) You, L.-Y.; Chen, S.-G.; Zhao, X.; Liu, Y.; Lan, W.-X.; Zhang, Y.; Lu,
H.-J.; Cao, C.-Y.; Li, Z.-T. Angew. Chem. Int. Ed. 2012, 51, 1657.
(17) (a) Chow, H.-F.; Lau, K.-N.; Ke, Z.; Liang, Y.; Lo, C.-M. Chem.
Commun. 2010, 3437. (b) Chow, H.-F.; Lo, C.-M.; Chen, Y. Top.
Heterocycl. Chem. 2012, 28, 137. (c) Chow, H.-F.; Chui, T.-K.; Qi,
Q. Synlett 2014, 25, 2246.
This work is supported by the UGC of HK (project no: AoE/P-03/08).
The 700 MHz NMR spectrometer was funded by the UGC of HKSAR
(SEG/CUHK09).
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Supporting Information
Supporting information for this article is available online at
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(18) Ke, Z.; Chow, H.-F.; Chan, M.-C.; Liu, Z.; Sze, K.-H. Org, Lett.
2012, 14, 394.
(19) Chow, H.-F.; Ng, K.-F.; Wang, Z.-Y.; Wong, C.-H.; Luk, T.; Lo, C.-M.;
Yang, Y.-Y. Org. Lett. 2006, 8, 471.
References and Notes
(20) See Supporting Information for details.
(1) Wynn, J. E.; Santos, W. L. Org. Biomol. Chem. 2015, 13, 5848.
(2) (a) Scully, C. C. G.; Jensen, P.; Rutledge, P. J. J. Organomet. Chem.
2008, 693, 2869. (b) Szyrwiel, Ł.; Szczukowski, Ł.; Pap, J. S.;
Setner, B.; Szewczuk, Z.; Malinka, W. Inorg. Chem. 2014, 53,
7951. (c) Lakatos, A.; Gyurcsik, B.; Nagy, N. V.; Csendes, Z.;
Wéber, E.; Fülöp, L.; Kiss, T. Dalton Trans. 2012, 41, 1713.
(3) Pap, J.; Szyrwiel, Ł.; Srankó, D.; Kerner, Z.; Setner, B.; Szewczuk,
Z.; Malinka, W. Chem. Commun. 2015, 51, 6322.
(4) (a) Boyce, R.; Li, G.; Nestler, P.; Suenaga, T.; Still, W. C. J. Am.
Chem. Soc. 1994, 116, 7955. (b) Davies, M.; Bonnat, M.; Guillier,
F.; Kilburn, J. D.; Bradley, M. J. Org. Chem. 1998, 63, 8696.
(c) Conza, M.; Wennemers, H. J. Org. Chem. 2002, 67, 2696.
(5) (a) Schneider, S. E.; O’Neil, S. N.; Anslyn, E. V. J. Am. Chem. Soc.
2000, 122, 542. (b) Kuchelmeister, H. Y.; Karczewski, S.;
Gutschmidt, A.; Knauer, S.; Schmuck, C. Angew. Chem. Int. Ed.
2013, 52, 14016.
(6) Wennemers, H. Chimia 2003, 57, 237.
(7) Ryadnov, M. G.; Woolfson, D. N. Angew. Chem. Int. Ed. 2003, 42,
3021.
(8) Gudlur, S.; Sukthankar, P.; Gao, J.; Avila, L. A.; Hiromasa, Y.;
Chen, J.; Iwamoto, T.; Tomich, J. M. PLoS One 2012, 7, e45374.
(9) Hanessian, S.; Vinci, V.; Fettis, K.; Maris, T.; Phan Viet, M. T.
J. Org. Chem. 2008, 73, 1181.
(10) For a review of peptide bond isosteres, see: Choudhary, A.;
Raines, R. T. ChemBioChem 2011, 12, 1801.
(21) Typical Experimental Procedure – Compound 2
Boc-V-Prg (56 mg, 0.22 mmol) and diazide 7 (57 mg, 0.1 mmol)
were dissolved in degassed THF. CuSO4·5H2O (5.5 mg, 22 μmol)
and sodium ascorbate (22 mg, 0.11 mmol) were then added, fol-
lowed by the addition of small amount of water. The reaction
mixture was stirred at 25 °C for 12 h. Saturated KHSO4 aqueous
solution was added to quench the reaction. THF was removed
under reduced pressure, and the remaining slurry aqueous layer
was extracted with EtOAc. The organic extracts were then com-
bined, washed with brine, dried over anhydrous Na2SO4, and
concentrated under reduced pressure. The crude product was
purified by flash column chromatography (hexane/EtOAc = 1:1)
to afford the product 2 (76 mg, 0.07 mmol, 71%) as a white
solid; 159–162 °C; Rf = 0.38 (EtOAc). 1H NMR (400 MHz, CDCl3):
δ = 8.01 (s, T′, 1 H), 7.96 (s, T, 1 H), 7.71 (br d, J = 7.5, LαNH, 1 H),
7.46 (br s, NH2 and NH2′, 2 H), 7.39 (br s, LεNH, 1 H), 5.49 (br d, J
= 8.7, BocNH or BocNH′, 1 H), 5.44 (br d, J = 8.8, BocNH′ or
BocNH, 1 H), 5.16 (d, J = 10.2, V1αCH, 1 H), 4.95 (d, J = 10.2,
V1′αCH, 1 H), 4.65–4.47 (m, CH2Triaz and LαCH, 5 H), 4.20–4.10
(m, V2αCH and V2′αCH, 2 H), 4.07–3.97 (m, OCH2, 2 H), 3.30–
3.19 (m, LεCHH, 1 H), 3.15–3.05 (m, LεCHH, 1 H), 2.60–2.45 (m, 2
H), 2.17–2.04 (m, 2 H), 1.80–1.70 (m, 1 H), 1.64–1.50 (m, 3 H),
1.50–1.44 (m, 3 H), 1.40 (s, C(CH3)3, 18 H), 1.35–1.26 (m, 6 H),
1.20–1.10 (m, 4 H), 1.11 (d, J = 6.4, CH3, 3 H), 1.05 (d, J = 6.4, CH3,
6 H), 0.94–0.85 (m, CH3, 21 H), 0.77 (d, J = 6.4, CH3, 3 H), 0.76 (d,
J = 6.4, CH3, 3 H). 13C NMR (100 MHz, CDCl3): δ = 172.3, 172.2,
171.8, 168.3, 168.2, 156.2, 144.6, 122.2, 122.0, 79.5, 70.1, 69.6,
68.1, 59.6, 52.3, 38.9, 37.6, 35.8, 35.7, 34.9, 32.2, 32.0, 31.5,
31.0, 28.7, 28.6, 28.3, 28.2, 22.6, 19.24, 19.16, 18.7, 18.0, 17.9;
[α] –7.4 (c 0.06, CHCl3); ESI-MS: m/z (%) = 1096 (100) [M + Na+].
ESI-HRMS: m/z calcd for C54H96N12O10 + Na+: 1095.7265; found:
1095.7297.
(11) Lauria, A.; Delisi, R.; Mingoia, F.; Terenzi, A.; Martorana, A.;
Barone, G.; Almerico, A. M. Eur. J. Org. Chem. 2014, 3289.
(12) Ramírez, M. A.; Martín, V. S.; Gallardo, A. G. Comput. Theor.
Chem. 2013, 1026, 31.
(13) (a) Horne, W. S.; Stout, C. D.; Ghadiri, M. R. J. Am. Chem. Soc.
2003, 125, 9372. (b) Horne, W. S.; Yadav, M. K.; Stout, C. D.;
Ghadiri, M. R. J. Am. Chem. Soc. 2004, 126, 15366. (c) Qin, S.-Y.;
Xu, X.-D.; Chen, C.-S.; Chen, J.-X.; Li, Z.-Y.; Zhuo, R.-X.; Zhang, X.-
Z. Macromol. Rapid Commun. 2011, 32, 758.
(22) Baxter, N. J.; Williamson, M. P.; Lilley, T. H.; Haslam, E. J. Chem.
Soc., Faraday Trans. 1996, 92, 231.
(23) Wang, Y.; Xiang, J.; Jiang, H. Chem. Eur. J. 2011, 17, 613.
(24) MacroModel, Version 10.9; Schrödinger, LLC: New York, NY,
2015.
(14) Zhan, J.; Tian, D.; Li, H. New J. Chem. 2009, 33, 725.
(25) Jaguar, Version 9.3; Schrödinger, LLC: New York, NY, 2016.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–E