D. K. Mohapatra et al. / Tetrahedron Letters 50 (2009) 5636–5639
5639
(CDCl3, 200 MHz): d 1.15–1.18 (d, 3H, J = 6.2 Hz), 1.47–1.74 (m, 4H), 2.17 (br s,
1H) 3.69–3.77 (m, 2H), 3.80 (s, 3H), 4.28 (d, 1H, J = 11.4 Hz), 4.54 (d, 1H,
J = 11.4 Hz), 5.17–5.26 (m, 2H), 5.75 (m, 1H), 6.85–6.89 (m, 2H), 7.23–7.27 (m,
2H); 13C NMR (CDCl3, 50 MHz) d 23.3, 31.8, 35.0, 55.0, 67.4, 69.6, 80.1, 113.6,
117.1, 129.3, 130.3, 138.7, 158.9; Anal. Calcd for C15H22O3: C, 71.97; H, 8.86.
Found: C, 71.94; H, 8.72.
129.2, 129.4, 130.0, 130.4, 138.9, 159.2, 170.3; Anal. Calcd for C26H32O6: C,
70.89; H, 7.32. Found: C, 70.72; H, 7.28.
20. Analytical and spectral data of 3: ½a D25
ꢁ
ꢀ9.5 (c 1.0, MeOH). 1H NMR (CD3OD,
500 MHz) (conformational isomers) d 1.16 (d, 1.5H, J = 6.6 Hz), 1.21 (d, 1.5H,
J = 6.9 Hz), 1.43 (dd, 0.5H, J = 6.8, 15.7 Hz), 1.62–1.74 (m, 2H), 1.76 (m, 0.5H),
1.90–2.01 (m, 1H), 2.29 (dd, 0.5H, J = 5.6, 13.4 Hz), 2.47–2.54 (m, 1H), 2.90 (dd,
0.5H, J = 7.5, 13.4 Hz), 4.39 (m, 1H), 4.54 (m, 1H), 4.69–4.75 (m, 2H), 5.00 (m,
1H), 5.39 (dd, 0.5H, J = 7.5, 16.2 Hz), 5.53 (dd, 0.5H, J = 8.2, 16.2 Hz), 5.78 (dd,
0.5H, J = 15.9 Hz), 5.88 (dd, 0.5H, J = 15.9 Hz); 13C NMR (CD3OD, 125 MHz)
(conformational isomers) d 18.9, 22.1, 28.6. 29.2, 32.6, 45.4, 45.8, 68.7, 69.1,
70.4, 72.4, 74.2, 130.7, 131.9, 138.2, 172.0, 172.5. Anal. Calcd for C10H16O4: C,
59.98; H, 8.05. Found: C, 60.15; H, 8.23.
16. (a) Inanga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc.
Jpn. 1979, 52, 1989; (b) Okino, T.; Qi, S.; Matsuda, H.; Murakami, M.;
Yamaguchi, K. J. Nat. Prod. 1997, 60, 158.
17. Analytical and spectral data of 6: ½a D25
ꢁ
ꢀ36.5 (c 1.0, CHCl3); IR (CHCl3, cmꢀ1):
3076, 3005, 2978, 2935, 2864, 1729, 1642, 1613, 1513, 1464, 1248, 1036, 994,
822, 756. 1H NMR (CDCl3, 200 MHz) d 1.16–1.19 (d, 3H, J = 6.3 Hz), 1.49–1.75 (m,
4H), 2.44 (dd, 1H, J = 5.7, 14.9 Hz), 2.63 (dd, 1H, J = 8.0, 14.9 Hz), 3.69 (m, 1H),
3.79 (s, 3H), 3.81 (s, 3H), 4.21 (m, 1H), 4.32 (d, 2H, J = 11.4 Hz), 4.52 (d, 2H,
J = 11.4 Hz), 4.90 (m, 1H), 5.14–5.35 (m, 4H), 5.60–5.86 (m, 2H), 6.82–6.88 (m,
4H), 7.20–7.26 (m, 4H); 13C NMR (CDCl3, 50 MHz) d 19.9, 31.0, 31.4, 41.3, 55.0,
69.6, 70.0, 70.7, 76.7, 79.4, 113.6, 117.1, 117.8, 129.1, 130.2, 130.5, 137.3,
138.7, 159.0, 170.2; Anal. Calcd for C28H36O6: C, 71.77; H, 7.74. Found: C, 71.68;
H, 7.64.
21. Analytical and spectral data of 4: ½a D25
ꢁ
ꢀ38.0 (c 0.74, MeOH); 1H NMR (500 MHz,
CD3OD) d 1.16 (d, 3H, J = 6.5 Hz), 1.44 (dd, 1H, J = 7.0, 15.9 Hz), 1.67 (br t, 1H,
J = 12.3 Hz), 1.83–1.95 (m, 2H), 2.32 (t, 1H, J = 10.4 Hz), 2.61 (dd, 1H, J = 5.2,
10.1 Hz), 4.32 (m, 1H), 4.35 (ddd, 1H, J = 5.2, 8.6, 10.6 Hz), 4.77 (m, 1H), 5.45 (br
d, 1H, J = 15.9 Hz), 5.73 (ddd, 1H, J = 1.6, 8.6, 15.9 Hz); 13C NMR (125 MHz,
CD3OD) d 22.5, 29.5, 36.5, 47.6, 69.2, 74.3, 74.9, 131.9, 134.8, 173.0; MS (ESI) m/z:
223.22(M++Na).
18. (a)Nicolaou, K. C.; Bulger, P. G.;Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490;(b)
Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199;(c)Prunet, J. Angew. Chem., Int.
Ed. 2003, 42, 2826; (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; (e)
Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012; (f) Maier, M. E. Angew. Chem.,
Int. Ed. 2000, 39, 2073; (g) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413; (h)
Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371; For a discussion of
strategic advantages related to RCM, see: (i) Furstner, A. Synth. Lett. 1999, 1523.
22. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.;
Cheeseman, J. R.; Jr. Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.;
Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.;
Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.;
Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao,
O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo,
C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi,
R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.;
Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.;
Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.;
Foresman, J. B.; Ortiz, J. V.; Cui, Q. A.; Baboul, G.; Clifford, S.; Cioslowski, J.;
Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.;
Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe,
M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.
GAUSSIAN 03, Revision C.1; Gaussian, Inc.: Pittsburgh, PA, 2003.
19. Analytical and spectral data of 20: ½a D25
ꢁ
ꢀ53.1 (c 1.0, CHCl3); IR (CHCl3, cmꢀ1):
2978, 2932, 2864, 1612, 1513, 1459, 1247, 1172, 1086, 1035, 821, 756. 1H NMR
(CDCl3, 500 MHz) d 1.14 (d, 3H, J = 6.6 Hz), 1.63–1.70 (m, 3H), 1.84 (m, 1H),
2.44 (dd, 1H, J = 7.3, 14.2 Hz), 2.91 (dd, 1H, J = 8.3, 14.2 Hz), 3.71 (m, 1H), 3.75
(2s, 6H), 4.24–4.29 (m, 2H), 4.35 (d, 1H, J = 11.5 Hz), 4.45 (d, 1H, J = 11.7 Hz),
4.50 (d, 1H, J = 11.5 Hz), 5.00 (m, 1H), 5.44 (dd, 1H, J = 8.5, 16.1 Hz), 5.61 (dd,
1H, J = 9.3, 16.1 Hz), 6.83–6.85 (m, 4H), 7.22–7.25 (m, 4H); 13C NMR (CDCl3,
125 MHz) d 18.6, 27.9, 29.9, 42.3, 55.2, 70.2, 71.0, 76.2, 79.2, 113.7, 128.9,