Synthetic transformations of higher terpenoids. XXXIV.∗ preparation of carboxyl derivatives of isopimaric acid

Chemistry of Natural Compounds

Volumn 50, Issue 4, 2014, Pages 673-680

  Timoshenko, M A ^a,b   Ayusheev, A B ^a,b   Kharitonov, Yu V ^a   Shakirov, M M ^a   Shul'ts, E E ^a  

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

^b NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

Author keywords

2 5 disubstituted oxazoles; 5 methyleneoxazoles; Bromination; Cycloisomerization; Isopimaric acid; N substituted amides

Indexed keywords

EID: 84911942405     PISSN: 00093130     EISSN: 15738388     Source Type: Journal    
DOI: 10.1007/s10600-014-1050-5     Document Type: Article

References (24)

1. Yu. V. Kharitonov, E. E. Shul'ts, and M. M. Shakirov, Chem. Nat. Compd., 49, 1067 (2014).
2. V. A. Pentegova, Zh. V. Dubovenko, V. A. Raldugin, and E. N. Shmidt, Conifer Terpenoids [in Russian], Izd. Nauka, Novosibirsk, 1987, 36 pp.
3. G. A. Tolstikov, T. G. Tolstikova, E. E. Shul'ts, S. E. Tolstikov, and M. V. Khvostov, Resin Acids of Russian Conifers. Chemistry and Pharmacology [in Russian], B. A. Trofimov (ed.), Geo, Novosibirsk, 2011, 395 pp.
4. W.-H. Li, S.-T. Chang, S.-C. Chang, and H.-T. Chang, Nat. Prod. Res., 22, 1085 (2008);
5. R. M. P. Gutierrez and E. G. Baez, J. Asian Nat. Prod. Res., 13, 934 (2011).
6. A. Bisio, D. Fraternale, G. Damonte, E. Millo, A. P. Lanteri, E. Russo, G. Romussi, B. Parodi, D. Ricci, and N. De Tommasi, Nat. Prod. Commun., 4, 1621 (2009).
7. E. M. Pferschy-Wenzig, O. Kunert, A. Presser, and R. Bauer, J. Agric. Food Chem., 56, 11688 (2008).
8. R. Tanaka, H. Tokuda, and Y. Ezaki, Phytomedicine, 15, 985 (2008).
9. K. Yamamoto, Y. Ueta, L. Wang, R. Yamamoto, N. Inoue, K. Inokuchi, A. Aiba, H. Yonekura, and N. Kato, J. Neurosci., 31, 11100 (2011);
10. J. Zaugg, S. Khom, D. Eigenmann, I. Baburin, M. Hamburger, and S. Hering, J. Nat. Prod., 74, 1764 (2011).
11. S. Janocha, J. Zapp, M. Hutter, M. Kleser, J. Bohlmann, and R. Bernhardt, ChemBioChem, 14, 467 (2013).
12. Y.-X. Chen, Z.-D. Zhao, Y. Gu, and Y.-J. Lu, Adv. Mater. Res., 634, 440 (2013).
13. J. P. Tresca, J. L. Fourrey, J. Polonsky, and E. Wemkert, Tetrahedron Lett., 12, 895 (1973).
14. N. V. Borisova, S. R. Kushnir, Yu. A. Kurskii, E. N. Shmidt, V. A. Dodonov, and B. A. Radbil', Khim. Rastit. Syr'ya, 2, 21 (2005).
15. V. S. C. Yeh, Tetrahedron, 60, 11195 (2004).
16. E. Riego, D. Hernandez, F. Albericio, and M. Alvarez, Synthesis, 12, 1907 (2005).
17. Z. Jin, Nat. Prod. Rep., 26, 382 (2009).
18. A. S. K. Hashmi, J. P. Weyrauch, W. Frey, and J. W. Bats, Org. Lett., 6, 4391 (2004);
19. J. P. Weyrauch, A. S. K. Hashmi, A. M. Schuster, T. Hengst, S. Schetter, A. Littmann, M. Rudolph, M. Hamzic, J. Visus, F. Rominger, W. Frey, and J. W. Bats, Chem. Eur. J., 16, 956 (2010);
20. A. O. Egorova, H. Seo, Y. Kim, D. Moon, Y. M. Rhee, and K. H. Ahn, Angew. Chem. Int. Ed., 50, 11446 (2011).
21. C. L. Paradise, P. R. Sarkar, M. Razzak, and J. K. De Brabander, Org. Biomol. Chem., 9, 4017 (2011).
22. G. C. Senadi, W.-P. Hu, J.-S. Hsiao, J. K. Vandavasi, C.-Y. Chen, and J.-J. Wang, Org. Lett., 14, 4478 (2012).
23. M. Tran-Dube, S. Johnson, and I. McAlpine, Tetrahedron Lett., 54, 259 (2013).
24. G. Brauer, Handbook of Preparative Inorganic Chemistry [Russian translation, 4, Mir, Moscow, 1985, pp. 1105, 1117].