5
944
D. K. Mohapatra et al. / Tetrahedron Letters 50 (2009) 5941–5944
2
5
); 1H NMR (300 MHz,
25
D
); 1H NMR (300 MHz,
3
3
7. Analytical and spectral data of 5: ½
a
ꢀ
+10.6 (c 1.08, CHCl
3
46. Analytical and spectral data of 3b: ½
CDCl
J = 10.4 Hz, 1H), 5.75 (m, 1H), 5.14 (d, J = 3.9, 2H), 5.10 (s, 1H), 2.58–2.51 (m,
a
ꢀ
ꢁ7.2 (c 0.5, CHCl
D
CDCl
3
) 7.27 (d, J = 8.7 Hz, 2H), 6.88 (d, J = 8.7 Hz, 2H), 4.46 (s, 2H), 3.80 s, 3H),
3
) 6.73 (m, 1H), 6.40 (d, J = 17.2 Hz, 1H), 6.14–6.05 (m, 2H), 5.84 (d,
3
1
6
1
.59 (t, J = 7.2 Hz, 2H), 3.06 (m, 1H), 2.78 (t, J = 4.7 Hz, 1H), 2.52 (m, 1H), 1.9 (m,
H), 1.76 (m, 1H); 13C NMR (75 MHz, CDCl
) 159.1, 130.28, 129.2, 113.8, 72.7,
6.7, 55.2, 47.1, 32.9; IR (neat): 3495, 2928, 2857, 1611, 1512, 1247,
13
3
3
2H), 2.40 (t, J = 6.4 Hz, 2H), 2.25 (s, 3H); C NMR (75 MHz, CDCl ) 198.2, 165.5,
142.5, 133.2, 132.7, 131.1, 128.3, 118.6, 71.6, 38.2, 36.6, 26.9; IR (neat): 3433,
2924, 2854, 1723, 1676, 1+633, 1407, 1262, 1191, 1048 cm
ꢁ
1
6
ꢁ1
097 cm ; MS (ES+, 3.99 ꢂ 10 ) m/z 209 [M+1].
;
MS (ES+,
5
3
3
4
8. Gaunt, M. J.; Jessiman, A. S.; Orsini, P.; Hook, D. F.; Tanner, H. R.; Ley, S. V. Org.
1.76 ꢂ 10 ) m/z 231 [M+Na] .
Lett. 2003, 5, 4819.
47. (a) Gradillas, A.; Pérez-Castells, J. Angew. Chem., Int. Ed. 2006, 45, 6086; (b)
Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490; (c)
Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199; (d) Prunet, J. Angew. Chem.,
Int. Ed. 2003, 42, 2826; (e) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34,
18; (f) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012; (g) Maier, M. E. Angew.
Chem., Int. Ed. 2000, 39, 2073; (h) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54,
4413; (i) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371; For a
discussion of strategic advantages related to RCM, see: (j) Furstner, A. Synth.
Lett. 1999, 1523.
9. Li, D.-R.; Zhang, D.-H.; Sun, C.-Y.; Zhang, J.-W.; Yang, L.; Chen, J.; Liu, B.; Su, C.;
Zhou, W.-S.; Lin, G.-Q. Chem. Eur. J. 2006, 12, 1185.
0. (a) Ohtani, I.; Kusumi, J.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113,
4
1
092; (b) Yoshido, W. Y.; Bryan, P. J.; Baker, B. J.; McClintock, J. B. J. Org. Chem.
995, 60, 780.
2
D
5
); 1H NMR (300 MHz,
4
1. Analytical and spectral data of 4: ½
a
ꢀ
+20.8 (c 0.5, CHCl
3
CDCl
3
) 7.19 (d, J = 8.7 Hz, 2H), 6.81 (d, J = 8.7 Hz, 2H), 6.35 (m, 2H), 6.07 (m,
13
1
H), 3.78 (s, 3H), 3.54–3.39 (m, 2H), 2.38–2.33 (m, 2H), 1.89–1.83 (m, 2H);
C
2
D
5
); 1H NMR (500 MHz,
3
NMR (75 MHz, CDCl
3
), 165.7, 159.1, 133.3, 130.4, 129.2, 128.6, 117.6, 113.7,
48. Analytical and spectral data of 1: ½
aꢀ
ꢁ46.5 (c 0.7, CHCl
7
1
3
2.7, 70.9, 66.1, 55.2, 38.8, 33.7; IR (neat): 3074, 2928, 2860, 1722, 1613, 1513,
CDCl ) 7.28 (m, 3H), 7.20 (m, 2H), 6.88 (ddd, J = 3.7, 4.5, 8.9 Hz, 1H), 6.80 (dt,
3
ꢁ
1
5
+
406, 1248, 1194, 1094, 1039 cm ; MS (ES+, 3.39 ꢂ 10 ) m/z 308 [M+NH
4
] ,
J = 7.4, 15.8 Hz, 1H), 6.20 (d, J = 15.8, 1H), 6.05 (d, J = 9.0 Hz, 1H), 4.55 (q, J = 6.8,
13.7 Hz, 1H), 2.93 (m, 2H), 2.91 (m, 2H), 2.64 (m, 2H), 2.33 (m, 2H); C NMR
+
13
13 [M+Na] .
4
4
4
4
2. Oikawa, Y.; Yushioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
3. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
4. Stjernschantz, J.; Resul, B. Drugs Future 1992, 17, 691.
(75 MHz, CDCl
3
) 199.0, 163.7, 144.6, 141.0, 140.0, 133.5, 128.5, 128.4, 126.1,
121.5, 76.1, 41.7, 29.9, 28.9; IR (neat): 3448, 2922, 2852, 1720, 1671, 1632,
ꢁ
1
6
1457, 1382, 1247, 1042 cm ; MS (ES+, 1.21 ꢂ 10 ) m/z 271 [M+1], 288
2
5
); 1H NMR (300 MHz,
+
+
5. Analytical and spectral data of 3a: ½
a
ꢀ
ꢁ6.0 (c 0.3, CHCl
3
[M+NH
49. Analytical and spectral data of 2: ½
CDCl ) 6.94–6.71 (m, 2H), 6.19 (d, J = 16.1, 1H), 6.06 (dt, J = 1.7, 9.8 Hz, 1H),
4.62 (m, 1H), 2.71–2.64 (m, 2H), 2.41–2.36 (m, 2H), 2.28 (s, 3H); C NMR
(75 MHz, CDCl ) 198.1, 163.7, 144.7, 140.8, 134.3, 121.4, 76.1, 37.5, 29.0, 27.0;
IR (neat): 3446, 2923, 2853, 1719, 1673, 1631, 1425, 1383, 1248,
4
] , 293 [M+Na] .
D
2
5
); 1H NMR (300 MHz,
CDCl ) 7.32–7.26 (m, 3H), 7.21–7.18 (m, 2H), 6.74 (m, 1H), 6.39 (dd, J = 1.4,
3
a
ꢀ
ꢁ35.4 (c 1.4, CHCl
3
D
1
5
2
1
2
2
7.2 Hz, 1H), 6.17–6.04 (m, 2H), 5.83 (dd, J = 1.2, 10.2 Hz, 1H), 5.74 (m, 1H),
3
13
.14–5.06 (m, 3H), 2.97–2.82 (m, 4H), 2.56–2.47 (m, 2H), 2.37 (t, J = 6.6 Hz,
H); 13C NMR (75 MHz, CDCl
) 199.1, 165.5, 141.6, 132.8, 132.7, 131.1, 128.5,
28.3, 126.1, 118.5, 71.7, 41.7, 38.1, 36.5, 30.0, 29.7; IR (neat): 3429, 3028,
3
3
ꢁ
1
ꢁ1
6
+
921, 2852, 1723, 1674, 1634, 1406, 1268, 1191, 1+ 048 cm
;
MS (ESI+,
1149, 1042 cm ; MS (ES+, 1.05 ꢂ 10 ) m/z 181 [M+1], 198 [M+NH
4
] , 203
5
+
+
.46 ꢂ 10 ) m/z 299 [M+1], 316 [M+NH
4
] , 321 [M+Na] .
[M+Na] .