Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives

ChemistryOpen

Volumn 5, Issue 1, 2016, Pages 65-70

  Timoshenko, Mariya A ^a,b   Kharitonov, Yurii V ^a,b   Shakirov, Makhmut M ^a   Bagryanskaya, Irina Yu ^a,b   Shults, Elvira E ^a,b  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

allylic amination reaction; diterpenoids; gold catalysis; pimaranes; stereoselectivity

Indexed keywords

ANILINE; GOLD; NUCLEOPHILES;

ALLYLIC AMINATION; ALLYLIC AMINATION REACTION; AMINATION REACTION; DITERPENOIDS; GOLD CATALYSIS; ISOPIMARIC ACIDS; NITROANILINES; PIMARANE; SYNTHETIC STUDY; TRIFLUOROMETHYL;

CATALYSIS;

EID: 84959545685     PISSN: None     EISSN: 21911363     Source Type: Journal    
DOI: 10.1002/open.201500187     Document Type: Article

References (47)

1. B. Hamberger, T. Ohnishi, B. Hamberger, A. Séguin, J. Bohlmann, Plant Physiol. 2011, 157, 1677-1695;
2. G. A. Tolstikov, T. G. Tolstikova, E. E. Shults, S. E. Tolstikov, M. V. Khvostov, Resin Acids from Ruissian Forest Conifers. Chemistry and Pharmacology (Ed.:, B. A. Trofimov,), Academic Publishing House GEO, Novosibirsk 2011, pp. 207-242.
3. E. Smith, E, Williamson, M. Zloh, S. Gibbons, Phytother. Res. 2005, 19, 538-542;
4. R. M. Perez Gutierrez, E. Garcia Baez, J. Asian Nat. Prod. Res. 2011, 13, 934-941;
5. S. S. Cheng, S. T. Chang, Wood Sci. Technol. 2014, 48, 831-840.
6. R. Tanaka, H. Tokuda, Y. Ezaki, Phytomedicine 2008, 15, 985-992;
7. G.-J. Zhang, Y.-H. Li, J.-D. Jiang, S.-S. Yu, J. Qu, S.-G. Ma, Y.-B. Liu, D.-Q. Yu, Tetrahedron 2013, 69, 1017-1023.
8. N. N. Ulusu, D. Ercil, M. K. Sakar, E. F. Tezcan, Phytother. Res. 2002, 16, 88-90.
9. E. M. Pferschy-Wenzig, O. Kunert, A. Presser, R. Bauer, J. Agric. Food Chem. 2008, 56, 11688-11693;
10. F. Gelmini, G. Beretta, C. Anselmi, M. Centini, P. Magni, M. Ruscica, A. Cavalchini, R. M. Facino, Int. J. Pharm. 2013, 440, 170-178.
11. Y. Imaizumi, K. Sakamoto, A. Yamada, A. Hotta, S. Ohya, K. Muraki, M. Uchiyama, T. Ohwada, Mol. Pharmacol. 2002, 62, 836-846.
12. S. W. Seto, A. L. S. Au, T. Y. Lam, S. S. C. Chim, S. M. Y. Lee, S. Wan, D. C. S. Tjiu, N. Shigemura, A. P. C. Yim, S. W. Chan, Br. J. Pharmacol. 2007, 151, 987-997;
13. C. Wu, K. V. Gopal, T. J. Lukas, G. W. Gross, E. J. Moore, Eur. J. Pharmacol. 2014, 732, 68-75;
14. L. Wang, H. Kang, Y. Li, Y. Shui, R. Yamamoto, T. Sugai, N. Kato, Neuropharmacology 2015, 92, 8-15.
15. W. Herz, A. L. Hall, J. Org. Chem. 1974, 39, 11-14;
16. B. Papillaud, F. Tiffon, M. Taran, A.-S. Miguel, B. Delmond, Tetrahedron 1985, 41, 1845-1857;
17. A. Feliciano, M. Medarde, E. Cabellero, F. Tome, B. Hebrero, J. Chem. Soc. Perkin Trans. 1 1992, 1665-1669.
18. Yu. V. Kharitonov, M. M. Shakirov, E. E. Shults, Chem. Nat. Compd. 2014, 49, 1067-1075.
19. M. Bordell Martín, A. Fernández Mateos, R. Rubio González, J. Chem. Soc. Perkin Trans. 1 1995, 569-576;
20. M. Medarde, E. Caballero, F. Tomé, A. S. Feliciano, Pharm. Biol. 2001, 39, 53-62;
21. Y. X. Chen, Z. D. Zhao, Y. Gu, Y. J. Lu, Adv. Mat. Res. 2013, 634-638, 440-444.
22. J. P. Tresca, J. L. Fourrey, J. Polonsky, E. Wemkert, Tetrahedron Lett. 1973, 14, 895-898.
23. M. A. Timoshenko, A. B. Ayusheev, Yu. V. Kharitonov, M. M. Shakirov, E. E. Shul′ts, Chem. Nat. Compd. 2014, 50, 673-680.
24. E. Emer, R. Sinisi, M. G. Capdevila, D. Petruzziello, F. De Vincentiis, P. G. Cozzi, Eur. J. Org. Chem. 2011, 647-666;
25. B. Biannic, A. Aponick, Eur. J. Org. Chem. 2011, 6605-6617;
26. A. Baeza, C. Nájera, Synthesis 2014, 46, 25-34.
27. G.-W. Wang, Y.-B. Shen, X.-L. Wu, Eur. J. Org. Chem. 2008, 4367-4371.
28. S. Shirakawa, S. Shimizu, Synlett 2008, 1539-1542.
29. P. Trillo, A. Baeza, C. Nájera, Eur. J. Org. Chem. 2012, 2929-2934.
30. H. B. Qin, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. Int. Ed. 2007, 46, 409-413;
31. Angew. Chem. 2007, 119, 413-417.
32. H. Yang, L. Fang, M. Zhang, C. Zhu, Eur. J. Org. Chem. 2009, 666-668.
33. X. Giner, P. Trillo, C. Nájera, J. Organomet. Chem. 2011, 696, 357-361;
34. B. Ranieri, I. Escofeta, A. M. Echavarren, Org. Biomol. Chem. 2015, 13, 7103-7118.
35. S. Guo, F. Song, Y. Liu, Synlett 2007, 964-968;
36. T. Ohshima, Y. Nakahara, J. Ipposhi, Y. Miyamoto, K. Mashima, Chem. Commun. 2011, 47, 8322-8324.
37. P. Mukherjee, R. A. Widenhoefer, Org. Lett. 2010, 12, 1184-1187;
38. P. Mukherjee, R. A. Widenhoefer, Angew. Chem. Int. Ed. 2012, 51, 1405-1407;
39. Angew. Chem. 2012, 124, 1434-1436;
40. P. Mukherjee, R. A. Widenhoefer, Chem. Eur. J. 2013, 19, 3437-3444.
41. B. Sreedhar, P. S. Reddy, M. A. Reddy, B. Neelima, R. Arundhathi, Tetrahedron Lett. 2007, 48, 8174-8177.
42. F. H. Allen, O. Kenard, D. G. Watson, L. Bramer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 2 1987, S 1-S 19.
43. G. M. Sheldrick, SHELX-97, Programs for Crystal Structure Analysis (Release 97-2), University of Göttingen, Göttingen (Germany), 1997.
44. SADABS, v. 2008-1, Bruker AXS, Madison, WI, USA, 2008.
45. A. L. Spek, PLATON, A Multipurpose Crystallographic Tool (Version 10M), Utrecht University, Utrecht (The Netherlands), 2003;
46. A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.
47. C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, J. van de Stree, J. Appl. Crystallogr. 2006, 39, 453-457.