6158
R. G. Brinson, P. B. Jones / Tetrahedron Letters 45 (2004) 6155–6158
9. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl.
Acknowledgements
1978, 17, 476–486.
10. Data for 8a: mp 154–155 ꢁC. 1H NMR (300 MHz, CDCl3)
d: 2.32–2.41 (m, 2H), 2.51–2.71 (m, 1H), 2.72–2.80 (m,
1H), 3.95–4.16 (m, 2H), 5.27–5.39 (m, 3H), 5.83–5.96 (m,
1H), 6.47–6.50 (d, J ¼ 9:0 Hz, 1H), 7.31–7.32 (d,
J ¼ 2:6 Hz, 1H), 7.36–7.54 (m, 5H), 7.94–7.98 (dd,
J ¼ 2:6, 9.0 Hz). 13C NMR (75 MHz, CDCl3) d: 147.0,
140.2, 137.1, 131.7, 130.0, 128.6, 128.4, 127.0, 125.3, 121.4,
117.5, 109.8, 89.7, 87.5, 51.1, 40.6, 36.1. Anal. Calcd for
C17H18N2O3: C, 70.79; H, 5.63; N, 8.69. Found: C, 70.36;
H, 5.64; N, 8.53.
We thank Dr. Marcus Wright for assistance with
acquisition and interpretation of NMR data. We also
thank the ACS Petroleum Research Fund (Grant
#37882-G4) and the North Carolina Biotechnology
Center (Grant #2001-ARG-0009) for funding.
References and notes
11. Data for 11a: 1H NMR (300 MHz, CDCl3) d: 1.74 (s, 3H),
1.81–1.95 (m, 1H), 2.01–2.11 (m, 1H), 2.17–2.30 (m, 2H),
3.77–3.99 (m, 2H), 5.13–5.19 (m, 2H), 5.26–5.33 (m, 1H),
5.87–5.99 (m, 1H), 6.64–6.67 (d, J ¼ 8:1 Hz, 1H), 6.69–
6.74 (td, J ¼ 0:9, 7.5 Hz, 1H), 7.03–7.13 (m, 2H). 13C
NMR (75 MHz, CDCl3) d: 142.3, 135.0, 131.7, 127.8,
122.9, 118.0, 116.4, 114.7, 90.1, 82.1, 54.8, 43.1, 34.2, 22.2.
Anal. Calcd. for C14H17NO: C, 78.10; H, 8.11; N, 6.51.
Found: C, 77.87; H, 7.84; N, 6.40.
1. Gentles, R. G.; Middlemiss, D.; Proctor, G. R.; Sneddon,
A. H. J. Chem. Soc., Perkin Trans. 1 1991, 6, 1423–1431.
2. Petterson, I.; Liljefors, T.; Bodeso, K. J. Med. Chem. 1990,
33, 2197–2204.
3. Peglion, J. L.; Vian, J.; Gourment, B.; Despaux, N.;
Audinot, V.; Millan, M. Bioorg. Med. Chem. Lett. 1997, 7,
881–886.
4. Ren, H.; Grady, S.; Gamenara, D.; Heinzen, H.; Moyna,
P.; Croft, S.; Kendrick, H.; Yardley, V.; Moyna, G.
Bioorg. Med. Chem. Lett. 2001, 11, 1851–1854.
5. Okada, E.; Tomifuji, T.; Tone, H.; Takeuchi, H.; Hojo, M.
Heterocycles 1998, 47, 143–148.
6. Noguchi, M.; Yamada, H.; Takamura, S.; Okada, K.;
Kakehi, A.; Yamamoto, H. Tetrahedron 2000, 56, 1299–
1307.
12. Honda, M.; Morita, H.; Nagakura, I. J. Org. Chem. 1997,
62, 8932–8936.
1
13. Data for 13: mp 200 ꢁC dec. H NMR (300 MHz, CDCl3)
d: 2.27–2.48 (m, 2H), 2.52–2.62 (m, 1H), 2.77–2.85 (m,
1H), 5.38 (br s, 1H), 5.54–5.58 (m, 1H), 6.52–6.55 (d,
J ¼ 8:7 Hz, 1H), 7.36–7.54 (m, 6H), 7.92–7.95 (dd,
J ¼ 2:6, 8.9 Hz, 1H). 13C NMR (75 MHz, CDCl3) d:
146.1, 140.1, 138.7, 130.5, 128.7, 128.4, 127.0, 124.8, 122.0,
113.8, 86.6, 83.8, 41.1, 37.0. Anal. Calcd. for C16H14N2O3:
C, 68.07; H, 5.00; N, 9.92. Found: C, 67.96; H, 4.95; N,
9.79.
7. Pedrosa, R.; Andres, C.; Roson, C. D.; Vicente, M. J. Org.
Chem. 2003, 68, 1852–1858.
8. Data for 2a: mp 78–79 ꢁC. 1H NMR (300 MHz, CDCl3) d:
2.12–2.36 (m, 2H), 2.42–2.54 (m, 2H), 3.83–4.08 (m, 2H),
5.19–5.24 (m, 1H), 5.30–5.37 (m, 1H), 5.50–5.52 (d,
J ¼ 5:8 Hz, 1H), 5.87–5.99 (m, 1H), 6.83–6.86 (dd,
J ¼ 0:6, 8.1 Hz, 1H), 7.26–7.32 (t, J ¼ 8:1 Hz, 1H), 7.47–
7.57 (m, 2H), 7.63–7.69 (m, 1H), 7.85–7.88 (m, 1H), 8.21–
8.24 (m, 1H). 13C NMR (75 MHz, CDCl3) d: 184.2, 142.9,
141.6, 133.8, 133.4, 131.2, 130.4, 128.8, 128.5, 128.1, 127.0,
124.4, 117.6, 116.9, 116.4, 91.1, 78.7, 53.9, 47.6, 35.9. Anal.
Calcd for C20H17NO2: C, 79.19; H, 5.65; N, 4.62. Found:
C, 78.95; H, 5.58; N, 4.55.
14. Data for 20: mp 93–95 ꢁC. 1H NMR (300 MHz, CDCl3) d:
2.40 (dd, J ¼ 9:0, 12.9 Hz, 1H), 2.93 (m, 1H), 3.02 (s, 3H),
3.03 (s, 3H), 3.44 (dd, J ¼ 4:8, 9.0 Hz, 1H), 5.54 (d,
J ¼ 6:0 Hz, 1H), 6.85 (d, J ¼ 0:9, 8.1 Hz, 1H), 7.55 (m,
5H), 8.23 (dd, J ¼ 1:2, 7.8 Hz, 1H). 13C NMR (75 MHz,
CDCl3) d: 184.1, 171.5, 158.6, 141.8, 139.0, 132.6, 131.9,
129.8, 129.2, 128.7, 127.3, 124.7, 117.6, 116.6, 92.2, 81.2,
60.9,
51.7,
37.5,
37.1.
HRMS
calcd
for
(C20H17NO4 + Naþ): 358.104977. Found: 358.10548.