Synthetic studies toward nortriterpenoids of schisandraceae family. Approach to the construction of functionalized C/D and A/B ring units of micrandilactone C and rubrifloradilactone B

Tetrahedron Letters

Volumn 52, Issue 48, 2011, Pages 6473-6476

  Hossain, Md Firoj ^a   Matcha, Kiran ^a   Ghosh, Subrata ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Diels Alder reaction; Lactone; Metathesis; Terpenoids

Indexed keywords

BICYCLO COMPOUND; BROMINE DERIVATIVE; MICRANDILACTONE C; RUBRIFLORADILACTONE B; TRITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; ETHERIFICATION; FEASIBILITY STUDY; NONHUMAN; REACTION ANALYSIS; SCHISANDRACEAE; SYNTHESIS;

ALNUS; SCHISANDRA; SCHISANDRACEAE;

EID: 80255132074     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.104     Document Type: Article

References (41)

1. Xiao, W. L.; Li, R. T.; Huang, S. X.; Pu, J. X.; Sun, H. D. Nat. Prod. Rep. 2008, 25, 871-891(b)
2. (a) Cheng, Y.-B.; Liao, T.-C.; Lo, I.-W.; Chen, Y.-C.; Kuo, Y.-C.; Chen, S.-Y.; Chie n, C.-T.; Shen, Y.-C. Org. Lett. 2010, 12, 1016-1019;
3. (c) Meng, F.-Y.; Sun, J.-X.; Li, X.; Yu, H.-Y.; Li, S.-M.; Ruan, H.-L. Org. Lett. 2011, 13, 1502-1505;
4. (d) Shi, Y.-M.; Li X.-Y.; Li, X.-N.; Luo, X.; Xue, Y.-B.; Liang, C.-Q.; Zou, J.; kong, L.-M.; Li, Y.; Pu, J.-X.; Xiao, W.-L.; Sun, H.-D. Org. Lett. 2011, 13, 3848-3851.
5. Li, R. T.; Han, Q. B.; Zheng, Y. T.; Wang, R. R.; Yang, L. M.; Lu, Y.; Sang, S. Q.; Zheng, Q. T.; Zhao, Q. S.; Sun, H. D. Chem. Commun. 2005, 2936-2938.
6. Li, R. T.; Li, S. H.; Zhao, Q. S.; Lin, Z. W.; Sun, H. D.; Lu, Y.; Wang, C.; Zheng, Q. T. Tetrahedron Lett. 2003, 44, 3531-3534.
7. (a) Tang, Y.; Zhang, Y.; Dai, M.; Luo, T.; Deng, L.; Chen, J.; Yang, Z. Org. Lett. 2005, 7, 885-888;
8. (b) Zhang, Y. D.; Tang, Y. F.; Luo, T. P.; Shen, J.; Chen, J. H.; Yang, Z. Org. Lett. 2006, 8, 107-110;
9. (c) Krishnan, K. S.; Smitha, M.; Suresh, E.; Radhakrishnan, K. V. Tetrahedron 2006, 62, 12345-12350;
10. (d) Fischer, D.; Theodorakis, E. A. Eur. J. Org. Chem. 2007, 4193-4196;
11. (e) Zhang, Y. D.; Ren, W. W.; Lan, Y.; Xiao, Q.; Wang, K.; Xu, J.; Chen, J. H.; Yang, Z. Org. Lett. 2008, 10, 665-668;
12. (f) Wang, Q.; Chen, C. Org. Lett. 2008, 10, 1223-1226;
13. (g) Paquette, L. A.; Lai, K. W. Org. Lett. 2008, 10, 2111-2113;
14. (h) Lai, K. W.; Paquette, L. A. Org. Lett. 2008, 10, 2115-2118;
15. (i) Paquette, L. A.; Lai, K. W. Org. Lett. 2008, 10, 3781-3784;
16. (j) Mehta, G.; Bhat, B. A. Tetrahedron Lett. 2009, 50, 2474-2477;
17. (k) Mehta, G.; Bhat, B. A.; Kumara, T. H. S. Tetrahedron Lett. 2009, 50, 6597-6600;
18. (l) Mehta, G.; Bhat, B. A.; Kumara, T. H. S. Tetrahedron Lett. 2010, 51, 4069-4072;
19. (m) Matcha, K.; Maity, S.; Malik, C. K.; Ghosh, S. Tetrahedron Lett. 2010, 51, 2754-2757;
20. (n) Maity, S.; Matcha, K.; Ghosh, S. J. Org. Chem. 2010, 75, 4192-4200;
21. (o) Mehta, G.; Yaragorla, S. Tetrahedron Lett. 2011, 52, 4485-4489.
22. Cordonnier, M.-C. A.; Kan, S. B. J.; Anderson, E. A. Chem. Commun. 2008, 5818-5820.
23. (a) Oppolzer, W. Angew. Chem., Int. Ed. 1977, 16, 10-23;
24. (b) Brieger, G.; Bennett, J. N. Chem. Rev. 1980, 80, 63-97;
25. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183-234;
26. (d) Sing, V.; Iyer, S. R.; Pal, S. Tetrahedron 2005, 61, 9197-9231;
27. (e) Juhl, M.; Tanner, D. Chem. Soc. Rev. 2009, 38, 2983-2992.
28. (a) Wenkert, E.; Naemura, K. Synth. Commun. 1973, 3, 45-48;
29. (b) Tuckett, M. W.; Watkins, W. J.; Whitby, R. J. Tetrahedron Lett. 1998, 39, 123-126;
30. (c) Li, C.-C.; Liang, S.; Zhang, X.-H.; Xie, Z.-X.; Chen, J.-H.; Wu, Y.-D.; Yang, Z. Org. Lett. 2005, 7, 3709-3712;
31. (d) Page, P. C. B.; Jennens, D. C.; Farland, H. M. Tetrahedron Lett. 1997, 38, 6913-6916.
32. Harwood, L. M.; Ishikawa, T.; Phillips, H.; Watkin, D. Chem. Commun. 1991, 527-530.
33. Malik, C. K.; Yadav, R. N.; Drew, M. G. B.; Ghosh, S. J. Org. Chem. 2009, 74, 1957-1963.
34. Saito, Y.; Zevaco, T. A.; Agrofolio, L. A. Tetrahedron 2002, 58, 9593-9603.
35. (a) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2036-2056;
36. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450;
37. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043;
38. (d) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238;
39. (e) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527;
40. (f) Ghosh, S.; Ghosh, S.; Sarkar, N. J. Chem. Sci. 2006, 118, 223-235;
41. (g) Chattopadhyay, S. K.; Karmakar, S.; Biswas, T.; Majumdar, K. C.; Rahaman, H.; Roy, B. Tetrahedron 2007, 63, 3919-3952.(g)