Synthesis of anacardic acids by nucleophilic substitution on 2-aryloxazolines

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1937-1939

  Seijas, Julio A ^a   Vázquez Tato, M Pilar ^a   Martínez, M Pilar ^a   Santiso, Verónica ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Anacardic acid; Grignard reagent; Oxazoline

Indexed keywords

ANACARDIC ACID; OXAZOLINE DERIVATIVE;

ARTICLE; GRIGNARD REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 1242293805     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.127     Document Type: Article

References (29)

1. Tyman J.H.P. Chem. Soc. Rev. 8:1979;499-537.
2. Yeddanapalli P.V.J. Nature (London). 174:1954;604.
3. Tyman J.H.P. Synthetic and Natural Phenols. 1996;Elsevier, Amsterdam. pp 465-557.
4. Gill M. Nat. Prod. Rep. 1999;301-317.
5. Sontag B., Dasenbrock J., Arnold N., Steglich W. Eur. J. Org. Chem. 1999;1051-1055.
6. Kobayashi S., Hidaka S., Kawamura Y., Ozaki M., Hayase Y. J. Antibiot. 51:1998;323.
7. Kobayash S., Nakai H., Ikenishi Y., Sun W.-Y., Ozaki M., Hayase Y., Takeda R. J. Antibiot. 51:1998;328.
8. Ino A., Hasegawa Y., Murabayashi A. Tetrahedron Lett. 39:1998;3509.
9. Erikson K.L., Beutler J.A., Cardellina J.H. II, Boyd M.R. J. Org. Chem. 62:1997;8188.
10. Kasemura K., Nomura M., Tada T., Fujihara Y., Shimomura K. J. Oleo Sci. 51:2002;637-642.
11. Kubo I., Muroi H., Himejima M., Yamgiwa Y., Mera H., Tokuxhima K., Ohta S., Kamikawa T. J. Agric. Food Chem. 41:1993;1012.
12. Kubo I., Ochi M., Vieira P.C., Komatsu S. J. Agric. Food Chem. 41:1993;553.
13. Sullivan J.T., Richards C.S., Lloyd H.A., Krishna G. Planta Med. 44:1982;175.
14. Prithiviraj B., Manickam M., Singh U.P., Ray A.B. Can. J. Bot. 75:1997;207-211.
15. Mwalongo G.C.J., Mkayula L.L., Dawson-Andoh B., Mubofu E.B., Shields J., Mwingira B.A. Green Chem. 1999;13-16.
16. Balasubramanyam K., Swaminathan V., Ranganathan A., Kundu T.K. J. Biol. Chem. 278:2003;19134-19140.
17. Shimomura, K.; Nakatani, Y.; Nakamua, M.; Takamatsu, S.; Fujiwara, Y.; Nomura, M. JP 06329516, 1994; Chem. Abstr. 122, 196554.
18. Kowata, K.; Onishi, M. JP10036887, 1998; Chem. Abstr. 128, 181864.
19. Kuwata, K.; Konixhi, M. JP 10036884, 1998; Chem. Abstr. 128, 193997.
20. Tyman J.H.P., Visani N. Chem. Phys. Lipids. 85:1997;157-174.
21. Seijas J.A., Vázquez-Tato M.P., Castedo L., Estévez R.J., Ruiz M. J. Org. Chem. 57:1992;5283-5284.
22. Martínez M.M., Onega M.G., Seijas J.A., Vázquez-Tato M.P. Tetrahedron. 53:1997;14127-14130.
23. Meyers A.I., Gabel R., Mihelich E.D. J. Org. Chem. 43:1978;1372-1379.
24. Green I.R., Tocoli F.E. J. Chem. Res. (S). 2002;105-106.
25. Satoh M., Takeuchi N., Nishimura T., Ohta T., Tobinaga S. Chem. Pharm. Bull. 49:2001;18-22.
26. Satoh M., Takeuchi N., Fujita T., Yamazaki K., Tobinaga S. Chem. Pharm. Bull. 46:1998;1501-1505.
27. Ino A., Hasegawa Y., Murabayashi A. Tetrahedron Lett. 39:1998;3509-3512.
28. Tyman J.H.P., Visani N. Chem. Phys. Lipids. 85:1997;157-174.
29. Nishikawa A., Hashimoto Y., Shirai R. Tetrahedron Lett. 39:1998;7307-7308.