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X.L. Qi et al. / Chinese Chemical Letters 23 (2012) 661–664
References
[1] (a) P.E. Maligres, I. Houpis, K. Rossen, et al. Tetrahedron 53 (1997) 10983;
(b) P.G. Houghton, A. Molina, J. Houpis, et al. US 005723616A (1998).
[
[
[
[
2] E. Fischer, F. Jourdan, Ber. 16 (1883) 2241.
3] N. Boyer, P. Gloanec, G.D. Nanteuil, et al. Eur. J. Org. Chem. (2008) 4277.
4] P.X. Li, C.D. Evans, Y.Z. Wu, et al. J. Am. Chem. Soc. 130 (2008) 2351.
5] (a) H. Sugano, M. Miyoshi, J. Org. Chem. 41 (1976) 2352;
(b) H. Sajiki, K. Hattori, K. Hirota, J. Org. Chem. 63 (1998) 7990.
[
[
6] S. Crosignani, P.D. White, B. Linclau, J. Org. Chem. 69 (2004) 5897.
1
7] Data of compound 2 [5b]: H NMR (400 MHz, CDCl
3
): d 10.1 (s, 1H, COOH), 7.31–7.27 (m, 5H, 5 Â ArH), 5.52 (d, 1H, J = 7.6 Hz, NH),
13
3 3
4
.51–4.48 (m, 3H, ArCH
2
and H-2), 3.92–3.89 (m, 1H, H-3a), 3.72–3.69 (m, 1H, H-3b), 1.44 (s, 9H, 3 Â CH
); C NMR (100 MHz, CDCl
): d
1
74.7 (CO), 155.6 (CO, C-1), 137.3 (C), 128.3 (CH), 127.7 (CH), 127.5 (CH), 80.2 (C), 73.2 (CH
2
), 69.7 (CH
2
, C-3), 53.7 (CH, C-2), 28.2
À
1
À
1
+
); IR (KBr, nmax/cm ): 3438, 2979, 2624, 1719, 1505, 1367, 1164, 738 cm ; EIMS (m/z, %): 295 (M , < 1), 239 (2), 194 (3), 148
(
3 Â CH
13), 132 (6), 133 (5), 91 (100), 57 (49).
3
(
1
[
8] Data of compound 11 [6]: H NMR (400 MHz, CDCl
ArCH
3
): d 7.32 (m, 5H, 5 Â ArH), 5.73 (d, 1H, J = 8.0 Hz, NH), 5.17 (d, 2H, J = 1.6 Hz,
13
3
2
), 4.39 (s, 1H, CH, H-2), 3.98–3.94 (m, 1H, H-3a), 3.86–3.83 (m, 1H, H-3b), 3.45 (s, 1H, OH), 1.42 (s, 9H, 3 Â CH
100 MHz, CDCl ): d 170.8 (CO), 155.7 (CO, C-1), 135.2 (C), 128.4 (CH), 128.2 (CH), 127.9 (CH), 80.0 (C), 67.0 (CH ), 62.9 (CH
CH, C-2), 28.1 (3 Â CH
94 (8), 148 (30), 132 (13), 133 (11), 91 (100), 57 (49).
9] S.T. Chen, K.T. Wang, Synthesis (1989) 36.
); C NMR
, C-3), 55.7
); IR (KBr, nmax/cm ): 3365, 2979, 1693, 1520, 1369, 1165, 1062, 783 cm ; EIMS (m/z, %): 295 (M , <1), 239 (3),
(
(
3
2
2
À1
À1
+
3
1
[
[
[
10] V.J. Hruby, K.W. Ehler, J. Org. Chem. 35 (1970) 1690.
11] (a) Y. Nomura, T. Bando, Y. Takeuchi, et al. Bull. Chem. Soc. Jpn. 56 (1983) 3199;
(
b) A.H. Jackson, P. Smith, Tetrahedron 24 (1968) 2227.
1
12] Data of synthesized MK-677: in the literature, some of H NMR and C NMR signals appeared as pairs of peaks due to the presence of amide
13
[
1
13
1
rotamers. Here, the H and C NMR data of the two rotamers were also described. H NMR (400 MHz, CD
3
OD): d 7.38–7.22 (m, 12H), 7.22–
.18 (m, 3H), 7.06 (t, 1H, J = 7.2 Hz), 6.99 (t, 1H, J = 7.6 Hz), 6.80 (d, 1H, J = 7.6 Hz), 5.27–5.13 (m, 2H), 4.58–4.46 (m, 6H), 4.09–3.98 (m,
H), 3.93 (s, 4H), 3.87–3.74 (m, 4H), 3.26–3.17 (m, 2H), 2.97 (s, 3H), 2.95 (s, 3H), 2.89–2.80 (m, 2H), 2.73 (s, 6H), 1.98–1.92 (m, 1H), 1.87–
7
2
1
13
3
.65 (m, 5H), 1.65 (s, 5H), 1.62 (s, 9H); C NMR (100 MHz, CD OD): d 173.1 (173.0, CO), 170.2 (170.0, CO), 142.7 (142.6, C), 139.6 (139.4,
C), 139.3 (C), 129.9 (129.8, CH), 129.7 (129.6, CH), 129.2 (CH), 129.13 (129.07, CH), 125.0 (CH), 124.6 (CH), 114.5 (114.4, CH), 74.5 (74.3,
CH ), 71.0 (70.2, CH ), 60.3 (60.0, CH ), 58.5 (C), 58.4 (CH ), 51.6 (50.9, CH), 44.5 (44.4, CH ), 44.2 (C), 41.1 (40.8, CH ), 39.7 (CH ), 37.6
36.9, CH ), 34.7 (CH ), 24.4 (24.3, CH ), 24.2 (24.1, CH ).
2
2
2
2
2
2
3
(
2
3
3
3