Progress towards viridin: Synthesis of the pentacyclic furanosteroid ring system via o-benzoquinonoid cycloadditions

Chemical Communications

Volumn , Issue 19, 1999, Pages 1947-1948

  Souza, Fabio E S ^a   Rodrigo, Russell ^b  

^a UNIVERSITY OF WATERLOO   (Canada)

^b WILFRID LAURIER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; BENZOQUINONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS;

EID: 0033533810     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905731e     Document Type: Article

References (16)

1. For a recent review, see J. R. Hanson, Nat. Prod. Rep., 1995, 12, 381.
2. M. M. Blight and J. F. Grove, J. Chem. Soc., Perkin Trans. 1, 1986, 1317.
3. T. J. Pecher, H-P. Weber and S. Kis, J. Chem. Soc., Chem. Commun., 1972, 1061.
4. T. Okada, L. Sakuma, Y. Fukui, O. Hazeki and M. Ui, J. Biol. Chem. 1994, 269, 3563.
5. S. Sato, M. Nakada and M. Shibasaki, Tetrahedron Lett., 1996, 37, 6141.
6. S. Honzawa, T. Mizutani and M. Shibasaki, Tetrahedron Lett., 1999, 40, 311; C. A. Broka and B. Ruhland, J. Org. Chem., 1992, 57, 4888.
7. S. Honzawa, T. Mizutani and M. Shibasaki, Tetrahedron Lett., 1999, 40, 311; C. A. Broka and B. Ruhland, J. Org. Chem., 1992, 57, 4888.
8. R. Carlini, K. Higgs, C. Older, S. Randhawa and R. Rodrigo, J. Org. Chem., 1997, 62, 2330.
9. O. Baine, G. F. Adamson, J. W. Barton, J. L. Fitch, D. R. Swayampati and H. Jeskey, J. Org. Chem., 1954, 19, 510. We thank Warren Wallace for laboratory assistance with the preparation of 9.
10. 4 catalysed reaction of 3-bromo-5-methylsalicyclic acid with NaOH: D. D. Weller and E. P. Stirchak, J. Org. Chem., 1983, 48, 4873. We were unable to obtain good yields of 9 by this method in spite of several attempts.
11. Prepared from 1-iodohepta-4,6-diene and silver nitrite in 68% yield; see E. Vedejs, T. H. Eberlein and R. G. Wilde, J. Org. Chem., 1988, 53, 2220 for the synthesis of the iodide.
12. R. Carlini, C-L. Fang, D. Herrington, K. Higgs, R. Rodrigo and N. Taylor, Aust. J. Chem., 1997, 50, 271.
13. A.P. Kozikowski and C-S. Li, J. Org. Chem., 1987, 52, 3541 and pertinent references therein.
14. D. P. Curran, J. Am. Chem. Soc., 1983, 105, 5826.
15. R. Carlini, K. Higgs, R. Rodrigo and N. Taylor, Chem. Commun., 1998, 65.
16. 3) 1.51 (s, Me), 2.18 (dd, J 17.8, 3.1, H-1α), 2.67 (m, H-15), 2.74 (dd, J 17.8, 2.3, H-1β), 3.67 (m, H-16), 4.00 (app dt, J 10.3, 2.6, H-4), 4.06 (dd, J 10.7, 8.1, H-20α), 4.87 (dd, J 9.8, 8.1, H-20β), 5.74 (app s, H-2, H-3), 7.55 (d, J 8.1, H-11), 7.89 (d, J 8.1, H-12). Full details will be published later.