Studies directed towards the synthesis of schisanartane and related complex nortriterpenoids: construction of models of the peripheral ABC and FGH segments of rubrifloradilactone C

Tetrahedron Letters

Volumn 51, Issue 31, 2010, Pages 4069-4072

  Mehta, Goverdhan ^a   Bhat, Bilal Ahmad ^a   Suresha Kumara, T H ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED RINGS WITH THREE OR MORE HETERO ATOMS; NORTRITERPENOID; RUBRIFLORADILACTONE C; TRITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRESS; CHEMICAL STRUCTURE; NONHUMAN; SCHISANDRACEAE;

EID: 77953960541     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.130     Document Type: Article

References (38)

1. Chang C.I., Kuo C.C., Chang J.Y., and Kuo Y.H. J. Nat. Prod. 67 (2004) 91-93
2. Li R., Shen Y., Xiang W., and Sun H. Eur. J. Org. Chem. (2004) 807-811
3. Li R.T., Xiao W.L., Shen Y.H., Zhao Q.S., and Sun H.D. Chem. Eur. J. 11 (2005) 2989-2996
4. Xiao W.L., Huang S.X., Zhang L., Tian R.R., Wu L., Li X.L., Pu J.X., Zheng Y.T., Lu Y., Li R.T., Zheng Q.T., and Sun H.D. J. Nat. Prod. 69 (2006) 650-653
5. Huang S.X., Li R.T., Liu J.P., Lu Y., Chang Y., Lei C., Xiao W.L., Yang L.B., Zheng Q.T., and Sun H.D. Org. Lett. 9 (2007) 2079-2082
6. Huang S.X., Yang J., Huang H., Li L.M., Xiao W.L., Li R.T., and Sun H.D. Org. Lett. 9 (2007) 4175-4178
7. Huang S.H., Yang L.B., Xiao W.L., Lei C., Liu J.P., Lu Y., Weng Z.Y., Li L.M., Li R.T., Yu J.L., Zheng Q.T., and Sun H.D. Chem. Eur. J. 13 (2007) 4816-4822
8. Lei C., Huang S.X., Chena J.J., Pu J.X., Li L.M., Xiao W.L., Liu J.P., Yang L.B., and Sun H.D. Helv. Chim. Acta 90 (2007) 1399-1405
9. Gao X.M., Pu J.X., Huang S.X., Lu Y., Lou L.G., Li R.T., Xiao W.L., Chang Y., and Sun H.D. J. Nat. Prod. 71 (2008) 1182-1188
10. Huang S.X., Han Q.B., Lei C., Pu J.X., Xiao W.L., Yu J.L., Yang L.M., Xu H.X., Zheng Y.T., and Sun H.D. Tetrahedron 64 (2008) 4260-4267
11. Xiao W.L., Lei C., Ren J., Liao T.G., Pu J.X., Pittman Jr. C.U., Lu Y., Zheng Y.T., Zhu H.J., and Sun H.D. Chem. Eur. J. 14 (2008) 11584-11592
12. Xiao W.L., Li R.T., Huang S.X., Pu J.X., and Sun H.D. Nat. Prod. Rep. 25 (2008) 871-891
13. Lei C., Huang S.X., Chen J.J., Yang L.B., Xiao W.L., Chang Y., Lu Y., Huang H., Pu J.X., and Sun H.D. J. Nat. Prod. 71 (2008) 1228-1232
14. Luo X., Chang Y., Zhang X.J., Pu J.X., Gao X.M., Wu Y.L., Wang R.R., Xiao W.L., Zheng Y.T., Lu Y., Chen G.Q., Zheng Q.T., and Sun H.D. Tetrahedron Lett. 50 (2009) 5962-5964
15. Xiao W.L., Gong Y.Q., Wang R.R., Weng Z.Y., Luo X., Li X.N., Yang G.Y., He F., Pu J.X., Yang L.M., Zheng Y.T., Lu Y., and Sun H.D. J. Nat. Prod. 72 (2009) 1678-1681
16. Cheng Y.B., Liao T.C., Lo I.W., Chen Y.C., Kuo Y.C., Chen S.Y., Chien C.T., and Shen Y.C. Org. Lett. 12 (2010) 1016-1019
17. Xiao W.L., Yang S.Y., Yang L.M., Yang G.Y., Wang R.R., Zhang H.B., Zhao W., Pu J.X., Lu Y., Zheng Y.T., and Sun H.D. J. Nat. Prod. 73 (2010) 221-225
18. Lei C., Xiao W.L., Huang S.X., Chen J.J., Pu J.X., and Sun H.D. Tetrahedron 66 (2010) 2306-2310
19. Tang Y., Zhang Y., Dai M., Luo T., Deng L., Chen J., and Yang Z. Org. Lett. 7 (2005) 885-888
20. Zhang Y.D., Tang Y.F., Luo T.P., Shen J., Chen J.H., and Yang Z. Org. Lett. 8 (2006) 107-110
21. Krishnan K.S., Smitha M., Suresh E., and Radhakrishnan K.V. Tetrahedron 62 (2006) 12345-12350
22. Fischer D., and Theodorakis E.A. Eur. J. Org. Chem. (2007) 4193-4196
23. Zhang Y.D., Ren W.W., Lan Y., Xiao Q., Wang K., Xu J., Chen J.H., and Yang Z. Org. Lett. 10 (2008) 665-668
24. Wang Q., and Chen C. Org. Lett. 10 (2008) 1223-1226
25. Paquette L.A., and Lai K.W. Org. Lett. 10 (2008) 2111-2113
26. Lai K.W., and Paquette L.A. Org. Lett. 10 (2008) 2115-2118
27. Paquette L.A., and Lai K.W. Org. Lett. 10 (2008) 3781-3784
28. Cordonnier M.C.A., Kan S.B.J., and Anderson E.A. Chem. Commun. (2008) 5818-5820
29. Matcha K., Maity S., Malik C.K., and Ghosh S. Tetrahedron Lett. 51 (2010) 2754-2757
30. Mehta G., and Bhat B.A. Tetrahedron Lett. 50 (2009) 2474-2477
31. Mehta G., Bhat B.A., and Kumara T.H.S. Tetrahedron Lett. 50 (2009) 6597-6600
32. +): 205.0841; found: 205.0831.
33. Rezgui F., and El Gaied M.M. Tetrahedron Lett. 39 (1998) 5965-5966
34. Luo S., Zhang B., He J., Janczuk A., Wang P.G., and Cheng J.-P. Tetrahedron Lett. 43 (2002) 7369-7371
35. -1, number of l.s. parameters = 247, R1 = 0.0607 for 2050 reflections with I > 2σ(I) and 0.1170 for all 3223 data. wR2 = 0.1147, GOF = 1.064 for all data, CCDC-764213. An ORTEP diagram of 33, drawn at 30% ellipsoidal probability, is shown below:{A figure is presented}
36. Semmelhack M.F., Schmid C.R., Cortes D.A., and Chou C.S. J. Am. Chem. Soc. 106 (1984) 3374-3376
37. Zhao M., Li J., Mano E., Song Z., Tschaen D.N., Grabowski E.J.J., and Rider P.J. J. Org. Chem. 64 (1999) 2564
38. Mehta G., and Roy S. Chem. Commun. (2005) 3210-3212