G. Chinna Reddy et al. / Bioorg. Med. Chem. Lett. 22 (2012) 2415–2417
2417
10. (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413; (b) Grubbs, R. H.
Tetrahedron 2004, 60, 7117.
Acknowledgments
11. (a) Corey, E. J.; Goto, G.; Marfat, A. J. Am. Chem. Soc. 1980, 102, 6607; (b)
Georges, Y.; Ariza, X.; Garcia, J. J. Org. Chem. 2008, 2009, 74.
The authors thank CSIR and UGC, New Delhi for financial assis-
tance. They are also thankful to NMR and Mass divisions of IICT for
spectral recording.
12. The spectral data of some selected compounds are given below. Compound 3:
½ ꢁ ;
a 2D5 = +32.4 (c = 2.4, CHCl3); IR: 3357, 1641, 1490, 1332 cmꢀ1 1H NMR
(200 MHz, CDCl3): d 7.45–7.36 (2H, m), 7.30–7.22 (3H, m), 5.81 (1H, m),
5.19–5.08 (2H, m), 4.88 (1H, br s), 4.22 (1H, m), 3.81 (1H, br s), 2.95 (H, br s),
2.32–2.22 (2H, m), 1.93–1.87 (2H, m); 13C NMR (50 MHz, CDCl3): d 134.2,
131.9, 128.5, 128.4, 122.8, 118.5, 89.9, 85.1, 68.3, 61.1, 42.2, 42.0; ESIMS: m/z
239 [M+Na]+; Anal. Calcd for C14H16O2: C, 77.78; H, 7.41. Found: C, 77.62; H,
7.38.
References and notes
1. (a) Juliawaty, L. D.; Kitajima, M.; Takayama, H.; Achmad, S. A.; Aimi, N.
Phytochemistry 2000, 54, 989; (b) Pereda-Miranda, R.; Fragoso-Serrano, M.;
Cerda-Garcia-Rojas, C. M. Tetrahedron 2001, 57, 47; (c) Boalino, D. M.; Connolly,
J. D.; Mclean, S.; Reynolds, W. F.; Tinto, W. F. Phytochemistry 2003, 64, 1303; (d)
Grkovic, T.; Blees, J. S.; Colburn, N. H.; Schmid, T.; Thomas, C. L.; Henrich, C. J.;
McMohan, J. B.; Gustafson, K. R. J. Nat. Prod. 2010, 74, 1015.
2. (a) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021; Hagen, S. E.; Vara Prasad, J. V.
N.; Tait, B. D. Adv. Med. Chem. 2000, 5, 159; (c) Jodynis-Liebert, J.; Murias, M.;
Bloszyk, E. Planta Med. 2000, 66, 199; (d) Murga, J.; Falomir, E.; García-Fortanet,
J.; Carda, M.; Marco, J. A. Org. Lett. 2002, 4, 3447; (e) Inayat-Hussain, S.; Annuar,
B. O.; Din, L. B.; Ali, A. M.; Ross, D. Toxicol. In Vitro 2003, 17, 433.
3. (a) Cavalheiro, A. J.; Yoshida, M. Phytochemistry 2000, 53, 811; (b) Sturgeon, C.
M.; Cinel, B.; Diaz-Marrero, A. R.; McHardy, L. M.; Ngo, M.; Anderson, R. J.;
Roberge, M. Cancer Chemother. Pharmocol. 2008, 61, 407.
4. (a) Das, B.; Balasubramanyam, P.; Chinna Reddy, G.; Salvanna, N. Synthesis
2011, 3706; (b) Das, B.; Nagendra, S.; Reddy, Ch. R. Tetrahedron: Asymmetry
2011, 22, 1249.
5. (a) Das, B.; Kumar, D. N. Synlett 2011, 1285; (b) Das, B.; Satyalakshmi, G.;
Suneel, K. Synthesis 2011, 2437; (c) Das, B.; Krishnaih, M.; Nagendra, S.; Reddy,
Ch. R. Lett. Org. Chem. 2011, 8, 244.
Compound 12: ½a 2D5
ꢁ
= ꢀ6.6 (c = 0.7, CHCl3); IR: 3449, 1625, 1436, 1254 cmꢀ1
;
1H
NMR (200 MHz, CDCl3): d 7.43–7.35 (2H, m), 7.32–7.22 (3H, m), 5.81 (1H, m),
5.27–5.01 (2H, m), 4.92 (1H, t, J = 7.0 Hz), 4.71 (1H, br s), 4.49 (1H, m), 3.90 (1H,
m), 2.32–2.14 (2H, m), 1.99 (1H, m), 1.80 (1H, m), 1.68 (3H, s), 1.69–1.57 (2H,
m), 1.35 (3H, s); 13C NMR (50 MHz, CDCl3): d 134.9, 131.9, 128.5, 128.4, 123.8,
118.7, 95.2, 89.8, 85.2, 65.3, 61.4, 61.3, 42.9, 42.0, 41.7, 25.0, 24.8; ESIMS: m/z
323 [M+Na]+; Anal. Calcd for C19H24O3: C, 76.00; H, 8.00. Found: C, 76.21; H,
8.06.
Compound 13: ½a 2D5
ꢁ
= +49.0 (c = 0.8, CHCl3); IR: 1712, 1639, 1463, 1258 cmꢀ1
;
1H NMR (200 MHz, CDCl3): d 7.49–7.42 (2H, m), 7.38–7.29 (3H, m), 6.90 (1H,
m), 6.03 (1H, d, J = 8.0 Hz), 4.99 (1H, t, J = 7.0 Hz), 4.68 (1H, m), 4.51 (1H, m),
2.42–2.32 (2H, m), 1.98–1.88 (2H, m), 1.82–1.71 (2H, m), 1.70 (3H, s), 1.39 (3H,
s); 13C NMR (50 MHz, CDCl3): d 164.2, 145.1, 131.3, 128.4, 128.3, 124.0, 121.4,
100.4, 89.5, 86.0, 74.1, 62.0, 60.0, 42.0, 37.1, 29.6, 23.4; ESIMS: m/z 349
[M+Na]+; Anal. Calcd for C20H22O4: C, 73.62; H, 6.75. Found: C, 73.78; H, 6.71.
Compound 1:
½ ꢁ = +119.4 (c = 0.1, CH2Cl2); IR: 3444, 1709, 1630, 1388,
a 2D5
1256 cmꢀ1 1H NMR (200 MHz, CDCl3): d 7.41–7.20 (5H, m), 6.90 (1H, m), 6.56
;
(1H, d, J = 11.0 Hz), 6.03 (1H, d, J = 9.0 Hz), 5.81 (1H, dd, J = 110, 9.0 Hz), 4.98
(1H, m), 4.73 (1H, m), 4.40 (1H, m), 2.40–2.32 (2H, m), 1.91–1.78 (2H, m), 1.71–
1.53 (2H, m); 13C NMR (50 MHz, CDCl3): d 164.5, 145.4, 136.3, 133.6, 130.8,
128.7, 128.4, 127.4, 121.3, 74.9, 65.8, 64.6, 43.1, 42.1, 29.9; ESIMS: m/z 311
[M+Na]+; Anal. Calcd for C17H20O4: C, 70.83; H, 6.94. Found: C, 70.72; H, 6.90.
6. Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708.
7. Determined by Chiral HPLC. Column: chiralcel OB-H; mobile phase: isopropyl
alohol/hexane (10:90); flow rate: 1 mL/min; detection: PDA.
8. Mitsunobu, O. Synthesis 1981, 1.
9. Rychnovsky, D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.