Approach to the synthesis of (+)-ifforestine. Model studies directed at the tetracyclic framework

Heterocycles

Volumn 60, Issue 9, 2003, Pages 2023-2044

  Roos, Gregory H P ^a   Dastlik, Kim A ^b  

^a SULTAN QABOOS UNIVERSITY   (Oman)

^b MURDOCH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZOPINEDIONE; IFFORESTINE; PIPECOLIC ACID DERIVATIVE; PLANT TOXIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLIZATION; MODEL; STRUCTURE ANALYSIS; SYNTHESIS; SYNTHON;

EID: 0042236906     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-9810     Document Type: Article

References (25)

1. S. L. Everist, In 'Poisonous Plants of Australia', 2nd Edition; Angus & Robertson, Sydney, 1981, p. 452.
2. C. R. Huxtable, 'Veterinary Clinical Toxicology Proceedings', No. 103; Univ. of Sydney, 1987, p. 88.
3. S. M. Colegate, P. R. Dorling, C. R. Huxtable, T. J. Shaw, B. W. Skelton, and A. H. White, Aust. J. Chem., 1989, 42, 1249.
4. H. Matsumura, H. Hashizume, A. Matsushita, and M. Eigyo, European Patent 89114483.4, 1989 (Chem. Abstr., 1989, 113, 40740).
5. T. Nagasaka and Y. Koseki, J. Org. Chem., 1998, 63, 6797.
6. M. Mori, M. Kimura, Y. Uozumi, and Y. Ban, Tetrahedron Lett., 1985, 26, 5947.
7. T. W. Greene and P. G. M. Wuts, 'Protecting Groups in Organic Synthesis', 2nd Edition, John Wiley & Sons, New York, 1991, p. 315.
8. B. Witkop and C. M. Foltz, J. Am. Chem. Soc., 1957, 79, 192.
9. W. Leimgruber, A. D. Batcho, and R. C. Czajkowski, J. Am. Chem. Soc., 1968, 90, 5641.
10. A. Mostad, C. Romming, and B. Storm, Acta Chem. Scand. B, 1978, 32, 639.
11. C. G. Boojamra, K. M. Burow, L. A. Thompson, and J. A. Ellman, J. Org. Chem., 1997, 62, 1240.
12. W. B. Wright, Jr., H. J. Brabander, E. N. Greenblatt, I. P. Day, and R. A. Hardy, Jr., J. Med. Chem., 1978, 21, 1087.
13. D. E. Thurston and D. S. Bose, Chem. Rev., 1994, 94, 433.
14. R. H. Shapiro and M. J. Heath, J. Am. Chem. Soc., 1967, 89, 5734.
15. V. Snieckus, Chem. Rev., 1990, 90, 879.
16. G. Theodoridis, M. C. Manfredi, and J. D. Krebs, Tetrahedron Lett., 1990, 31, 6141.
17. P. Hewawasam and N. A. Meanwell, Tetrahedron Lett., 1994, 35, 7303.
18. S. Bengtsson and T. Hogberg, J. Org. Chem., 1989, 54, 4549.
19. W. C. Black, B. Guay, and F. Scheuermeyer, J. Org. Chem., 1997, 62, 758.
20. J. Bredt and H. Hof, Ber., 1900, 33, 21.
21. D. A. Evans, C. E. Sacks, W. A. Kleschick, and T. A. Taber, J. Am. Chem. Soc., 1979, 101, 6789.
22. R. J. Boeckman, Jr., A. B. Charette, T. Asberom, and B. H. Johnson, J. Am. Chem. Soc., 1991, 113, 5337.
23. F. A. Carey and R. M. Giuliano, J. Org. Chem., 1981, 46, 1366.
24. J. Suffert, J. Org. Chem., 1989, 54, 509.
25. M. Pena and J. K. Stille, J. Am. Chem. Soc., 1989, 111, 5417.