Recent advances in the chemistry of caryophyllene

Natural Product Reports

Volumn 15, Issue 2, 1998, Pages 187-204

  Collado, Isidro G ^a   Hanson, James R ^b   Macías Sánchez, Antonio J ^a  

^a UNIVERSITY OF CÁDIZ   (Spain)

^b UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARYOPHYLLENE; CHEMICAL ANALYSIS; CHEMICAL AND PHYSICAL PROPERTIES;

EID: 0031922985     PISSN: 02650568     EISSN: None     Source Type: Journal    
DOI: 10.1039/a815187y     Document Type: Review

References (43)

1. (a) Dictionary of Organic Compounds, 5th edn., Vol. 1, p. 1012, ref. C-00398;
2. (b) B. M. Fraga, Nat. Prod. Rep., 1997, 14, 145 and previous reviews.
3. (a) J. M. Greenwood, J. K. Sutherland and A. Torre, J. Chem. Soc., Chem. Commun., 1965, 410;
4. (b) M. A. McKervey and J. R. Wright, J. Chem. Soc., Chem. Commun., 1970, 117.
5. (a) A. V. Tkachev, Zh. Org. Khim., 1987, 23, 475 [J. Org. Chem. USSR (Engl. Transi.), 1988, 23, 393];
6. (a) A. V. Tkachev, Zh. Org. Khim., 1987, 23, 475 [J. Org. Chem. USSR (Engl. Transi.), 1988, 23, 393];
7. (b) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser and M. Noltemeyer, J. Am. Chem. Soc., 1995, 117, 9180.
8. O. Wallach and W. Walker, Liebigs Ann. Chem., 1892, 271, 285.
9. (a) H. N. Rydon, J. Chem. Soc., 1936, 593; 1937, 1340;
10. (a) H. N. Rydon, J. Chem. Soc., 1936, 593; 1937, 1340;
11. (b) A. Campbell and H. N. Rydon, J. Chem. Soc., 1953, 3002;
12. (c) T. L. Dawson and G. R. Ramage, J. Chem. Soc., 1950, 3523; 1951, 3382.
13. (c) T. L. Dawson and G. R. Ramage, J. Chem. Soc., 1950, 3523; 1951, 3382.
14. F. Sorm, P. Dolejs and D. Pliva, Collect. Czech. Chem. Commun., 1950, 15, 186; D. H. R. Barton and A. S. Lindsey, J. Chem. Soc., 1951, 2988.
15. F. Sorm, P. Dolejs and D. Pliva, Collect. Czech. Chem. Commun., 1950, 15, 186; D. H. R. Barton and A. S. Lindsey, J. Chem. Soc., 1951, 2988.
16. Y. Asahina and T. Tsukamoto, J. Pharm. Soc. Jpn., 1922, 463.
17. G. G. Henderson, R. O. O. McCrone and J. M. Robertson, J. Chem. Soc., 1929, 1368.
18. (a) A. Aebi, D. H. R. Barton, A. W. Burgstahler and A. S. Lindsey, J. Chem. Soc., 1954, 4659;
19. (b) D. H. R. Barton and A. Nickon, J. Chem. Soc., 1954, 4665;
20. (c) A. W. Lutz and E. B. Reid, J. Chem. Soc., 1954, 2265;
21. (d) D. H. R. Barton, T. Bruun and A. J. Lindsey, J. Chem. Soc., 1952, 2210.
22. J. M. Robertson and G. Todd, J. Chem. Soc., 1955, 1254.
23. A. Horeau and J. K. Sutherland, J. Chem. Soc. C, 1966, 247.
24. (a) J. L. Simonsen and D. H. R. Barton, The Terpenes, Cambridge University Press, London, 1952, Vol. III, p. 39;
25. (b) D. H. R. Barton and P. De Mayo, Quarterly Reviews, 1957, 11, 189.
26. (a) E. J. Corey, R. B. Mitra and H. Uda, J. Am. Chem. Soc., 1963, 85, 362;
27. (b) E. J. Corey, R. B. Mitra and H. Uda, J. Am. Chem. Soc., 1964, 86, 485.
28. H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto and E. Osawa, J. Chem. Soc., Perkin Trans, 1, 1995, 1200.
29. J. L. Gras, R. Maurin and M. Bertrand, Tetrahedron Lett., 1969, 40, 3533.
30. M. Bertrand and J. L. Gras, Tetrahedron, 1974, 30, 793.
31. (a) A. Kumar, A. Sing and D. Devprabhakara, Tetrahedron Lett., 1976, 2177;
32. (b) A. Kumar and D. Devprabhakara, Synthesis, 1976, 461.
33. J. E. McMurray and D. D. Miller, Tetrahedron Lett., 1983, 1885.
34. Y. Ohtsuka, S. Niitsuma, H. Tadokoro, T. Hayashi and T. Oishi, J. Org. Chem., 1984, 49, 2326.
35. H. Shirahama, E. Osawa, B. R. Chhabra, T. Shimokawa, T. Yokono, T. Kanaiwa, T. Amiya and T. Matsumoto, Tetrahedron Lett., 1981, 22, 1527.
36. G. Guella, G. Chiasera, I. N'Diaye and F. Pietra, Helv. Chim. Acta, 1994, 77, 1203.
37. A. V. Tkachev, V. I. Mamatyuk and G. V. Dubovenko, Izv. Sib. Old. Akad. Nauk SSSR, Ser. Khim. Nauk, 1986, 1, 88.
38. G. R. Ramage and R. Whitehead, J. Chem. Soc., 1954, 4336.
39. K. H. Schulte-Elte and G. Olhoff, Helv. Chim. Acta, 1971, 54, 370.
40. V. P. Gatilova, D. V. Korchagina, T. V. Rybalova, Yu. V. Gatilov, Zh. V. Dubovenko and V. A. Barkhash, Zh. Org. Khim., 1989, 25, 320.
41. (a) W. Parker, R. A. Raphael and J. S. Roberts, Tetrahedron Lett., 1965, 2313;
42. (b) W. Parker, R. A. Raphael and J. S. Roberts, J. Chem. Soc. C, 1969, 2634.
43. K. Yoshihara and Y. Hirose, Bull. Chem. Soc. Jpn., 1975, 48, 2078.