An efficient synthesis of 3,5-dimethoxyhomophthalic acid, a key intermediate for synthesis of natural isocoumarins

Journal of Heterocyclic Chemistry

Volumn 40, Issue 3, 2003, Pages 519-522

  Saeed, Aamer ^a   Rama, Nasim H ^a   Arfan, M ^a  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DIMETHOXYHOMOPHTHALIC ACID; 3,5 DIMETHOXYPHENYLACETIC ACID; ACHLISOCOUMARIN; AGRIMONOLIDE; HOMOPHTHALIC ACID; ISOCOUMARIN DERIVATIVE; PHENYLACETIC ACID DERIVATIVE; PHTHALIC ACID DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0038637238     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570400317     Document Type: Article

References (37)

1. R. D. Barry, Chem. Rev., 64, 229 (1964).
2. R. A. Hill, Prog. Chem. Nat. Prod., 49, 1 (1986).
3. E. Napolitano, Org. Prep. Proced. Int. 29, 631 (1997).
4. U. Sankawa in Comprehensive Natural Products Chemistry, 1, p. 17, 415-419, Elsevier Science Publishers Ltd., Amsterdam (1999).
5. J. Mercier and J. Kuc, J. Sci. Food Agric., 73, 60 (1997).
6. M. Ichihara, T. Hashimoto, I. Hira, Y. Takeda, S. Sasamura, S. Sakaura, R. Sato and A. Tajimai, Chem. Lett., 1495 (1989).
7. S. M. Afzal, R. Pike, N. H. Rama, L. R. Smith, E. S. Turner and W. B. Whalley, J. Chem. Soc. Perkin Trans. I, 81 (1978).
8. G. F. Grove and M. Pople, J. Chem. Soc. Perkin Trans. I, 337 (1979).
9. M. Yamato and K. Hashigaki, Chem Pharm Bull., 24, 200 (1976).
10. C. N. Lewis, J. Staunton and D. C. Sunter, J. Chem. Soc Perkin Trans. I, 747 (1976).
11. T. Sassa, H. Aoki, and K. Munakata, Tetrahedron Lett., 5703 (1968); K. Tanaka, A. Kobayashi, and K. Yamashita, Agric. Biol. Chem., 37, 669 (1973).
12. T. Sassa, H. Aoki, and K. Munakata, Tetrahedron Lett., 5703 (1968); K. Tanaka, A. Kobayashi, and K. Yamashita, Agric. Biol. Chem., 37, 669 (1973).
13. G.A. Elestad, F. M. Lovell, N. A. Perkinson, R. T. Haragreaves and W. J. McGahren, J. Org. Chem., 43, 2339 (1978).
14. G. Speranza, P. Manitto, P. Cassara and D. Monti, Phytochemistry, 33, 175 (1993).
15. M. Mizuno, S. Yoshida, M. Inuma, T. Tanaka, F. A. Long and K. Goto, Chem. Pharm. Bull., 38, 2075 (1990).
16. A.S. Feliciano, J. M. Miguel del Corral, L. M Canedo, and M. Medarde, Phytochemistry, 29, 945 (1990).
17. G. B. Henderson and R. A. Hill, J. Chem. Soc. Perkin Trans. I, 111 (1982).
18. N.H. Rama, A. Saeed and C. W. Bird, Liebigs Ann. Chem., 4, 711 (1995) ibid., 12, 1331 (1993); A. Saeed N. H. Rama, J. Chem. Soc. Pak., 15, 140 (1993).
19. N.H. Rama, A. Saeed and C. W. Bird, Liebigs Ann. Chem., 4, 711 (1995) ibid., 12, 1331 (1993); A. Saeed N. H. Rama, J. Chem. Soc. Pak., 15, 140 (1993).
20. N.H. Rama, A. Saeed and C. W. Bird, Liebigs Ann. Chem., 4, 711 (1995) ibid., 12, 1331 (1993); A. Saeed N. H. Rama, J. Chem. Soc. Pak., 15, 140 (1993).
21. K. Nozawa, M. Yamada, Y. Tsuda, K. I. Kawai and S. Nakajima, Chem Pham Bull., 29, 2491, 3486 (1981); H. Kaji, M. Yamada, K. Nozawa, K. I. Kawai and S. Nakajima, Org. Prep. Proceed. Int., 18, 253 (1986); A. Saeed, Monat. Chemie, 134, 457 (2003); A. Saeed, Helvetica Chim. Acta, 86, 377 (2003).
22. K. Nozawa, M. Yamada, Y. Tsuda, K. I. Kawai and S. Nakajima, Chem Pham Bull., 29, 2491, 3486 (1981); H. Kaji, M. Yamada, K. Nozawa, K. I. Kawai and S. Nakajima, Org. Prep. Proceed. Int., 18, 253 (1986); A. Saeed, Monat. Chemie, 134, 457 (2003); A. Saeed, Helvetica Chim. Acta, 86, 377 (2003).
23. K. Nozawa, M. Yamada, Y. Tsuda, K. I. Kawai and S. Nakajima, Chem Pham Bull., 29, 2491, 3486 (1981); H. Kaji, M. Yamada, K. Nozawa, K. I. Kawai and S. Nakajima, Org. Prep. Proceed. Int., 18, 253 (1986); A. Saeed, Monat. Chemie, 134, 457 (2003); A. Saeed, Helvetica Chim. Acta, 86, 377 (2003).
24. K. Nozawa, M. Yamada, Y. Tsuda, K. I. Kawai and S. Nakajima, Chem Pham Bull., 29, 2491, 3486 (1981); H. Kaji, M. Yamada, K. Nozawa, K. I. Kawai and S. Nakajima, Org. Prep. Proceed. Int., 18, 253 (1986); A. Saeed, Monat. Chemie, 134, 457 (2003); A. Saeed, Helvetica Chim. Acta, 86, 377 (2003).
25. K. Nozawa, S. Nakajima and K. I. Kawai, Chem. Pharm. Bull., 28, 1112 (1980); R. H. Carter, R. M. Colyer, R. A. Hill and J. Staunton, J. Chem. Soc. Perkin Trans. I, 1432 (1982); H. L. Slates, S. Weber and N. L. Wendler Chimia, 21, 468 (1967); J. Mukherjee, J. N. Chatterjea, and S. C. Sengupta, Indian J. Chem., 13, 859 (1975); R. N. Hurd and D. H. Shah, J. Org. Chem., 38, 610 (1973).
26. K. Nozawa, S. Nakajima and K. I. Kawai, Chem. Pharm. Bull., 28, 1112 (1980); R. H. Carter, R. M. Colyer, R. A. Hill and J. Staunton, J. Chem. Soc. Perkin Trans. I, 1432 (1982); H. L. Slates, S. Weber and N. L. Wendler Chimia, 21, 468 (1967); J. Mukherjee, J. N. Chatterjea, and S. C. Sengupta, Indian J. Chem., 13, 859 (1975); R. N. Hurd and D. H. Shah, J. Org. Chem., 38, 610 (1973).
27. K. Nozawa, S. Nakajima and K. I. Kawai, Chem. Pharm. Bull., 28, 1112 (1980); R. H. Carter, R. M. Colyer, R. A. Hill and J. Staunton, J. Chem. Soc. Perkin Trans. I, 1432 (1982); H. L. Slates, S. Weber and N. L. Wendler Chimia, 21, 468 (1967); J. Mukherjee, J. N. Chatterjea, and S. C. Sengupta, Indian J. Chem., 13, 859 (1975); R. N. Hurd and D. H. Shah, J. Org. Chem., 38, 610 (1973).
28. K. Nozawa, S. Nakajima and K. I. Kawai, Chem. Pharm. Bull., 28, 1112 (1980); R. H. Carter, R. M. Colyer, R. A. Hill and J. Staunton, J. Chem. Soc. Perkin Trans. I, 1432 (1982); H. L. Slates, S. Weber and N. L. Wendler Chimia, 21, 468 (1967); J. Mukherjee, J. N. Chatterjea, and S. C. Sengupta, Indian J. Chem., 13, 859 (1975); R. N. Hurd and D. H. Shah, J. Org. Chem., 38, 610 (1973).
29. K. Nozawa, S. Nakajima and K. I. Kawai, Chem. Pharm. Bull., 28, 1112 (1980); R. H. Carter, R. M. Colyer, R. A. Hill and J. Staunton, J. Chem. Soc. Perkin Trans. I, 1432 (1982); H. L. Slates, S. Weber and N. L. Wendler Chimia, 21, 468 (1967); J. Mukherjee, J. N. Chatterjea, and S. C. Sengupta, Indian J. Chem., 13, 859 (1975); R. N. Hurd and D. H. Shah, J. Org. Chem., 38, 610 (1973).
30. P. A. S. Smith and R. O. Kan, J. Am. Chem. Soc., 82, 45753 (1960); Org. Syn. Coll. Vol. 5, 612, 1051 (1960); D. S. Breslow, E. Baumgarten and C. R. Hauser, J. Am. Chem. Soc., 66,1286 (1944).
31. P. A. S. Smith and R. O. Kan, J. Am. Chem. Soc., 82, 45753 (1960); Org. Syn. Coll. Vol. 5, 612, 1051 (1960); D. S. Breslow, E. Baumgarten and C. R. Hauser, J. Am. Chem. Soc., 66,1286 (1944).
32. P. A. S. Smith and R. O. Kan, J. Am. Chem. Soc., 82, 45753 (1960); Org. Syn. Coll. Vol. 5, 612, 1051 (1960); D. S. Breslow, E. Baumgarten and C. R. Hauser, J. Am. Chem. Soc., 66,1286 (1944).
33. F. M. Hauser and R. P. Rhee, J. Am. Chem. Soc., 99, 4533, (1977); F. M. Hauser and R. P. Rhee, Synthesis, 245 (1977).
34. F. M. Hauser and R. P. Rhee, J. Am. Chem. Soc., 99, 4533, (1977); F. M. Hauser and R. P. Rhee, Synthesis, 245 (1977).
35. A. Bruggink and McKillop, Tetrahedron, 31, 2601 (1975).
36. A. Giroux, C. Nadeau and Y. Han, Tetrahedron Lett., 41, 7601 (2000).
37. H. W. Pinnick, W. E. Childers and B. S. Bal, Tetrahedron, 37, 2091 (1981).