Steps towards a practical synthesis of macrocyclic bisbenzylisoquinolines

Journal of Heterocyclic Chemistry

Volumn 42, Issue 4, 2005, Pages 647-659

  Al Hiari, Yusuf M ^a   Bennett, Stephen J ^a   Cox, Brian ^b,c   Davies, Robert J ^a   Khalaf, Abedawn I ^a   Waigh, Roger D ^a   Worsley, Alan J ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c NOVARTIS HORSHAM RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BISBENZYLISOQUINOLINE ALKALOID; HETEROCYCLIC COMPOUND; MACROCYCLIC COMPOUND; NATURAL PRODUCT; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONFORMATION; SYNTHESIS;

EID: 19644390052     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570420426     Document Type: Article

References (31)

1. A. Jossang, M. Leboeuf, A. Cave and T. Sevenet, J. Nat. Prod., 49, 1028 (1986).
2. K. T. Buck, in The Alkaloids, R. H. F. Manske, H. L. Holmes, and G. A. Cordell, eds, Academic Press, New York, NY, 30, 1987, pp 1-222.
3. M. Kulka, in The Alkaloids: Chemical and Biological Perspectives, R. H. F. Manske, H. L. Holmes, eds, Academic Press, New York, NY, 4, 1954, pp 199-247.
4. P. L. Schiff, J. Nat. Prod., 60, 934 (1997).
5. S. J. Partridge, P. F. Russell, G. C. Kirby, D. H. Bray, D. C. Warhurst, J. D. Phillipson, M. J. O'Neill and P. L. Schiff, J. Pharm. Pharmacol. (Suppl.), 41, 92 (1989).
6. S. J. Partridge, P. F. Russell, G. C. Kirby, D. H. Bray, D. C. Warhurst, J. D. Phillipson, M. J. O'Neill and P. L. Schiff, J. Pharm. Pharmacol. (Suppl.), 40, 53 (1988).
7. R. J. Davies, PhD thesis, University of Strathclyde, 1995.
8. H. Oilman and S. H. Eidt, J. Am. Chem. Soc., 78, 2633 (1956).
9. It is probable that nickel boride would accomplish this step very cleanly: M. R. Euerby and R. D. Waigh, Syn. Commun., 16, 779 (1986).
10. D. R. Gauthier, K. S. Zandi and K. J. Shea, Tetrahedron 54, 2289 (1998).
11. A. Rumbo, L. Castedo and J. L. Mascarenas, J. Org. Chem., 58, 5585 (1993).
12. M. J. Kurth, S. H. Tahir and M. M. Olmstead, J. Org. Chem., 55, 2286 (1990).
13. J. Castro, A. Moyano, M. A. Pericas and A. Riera, J. Org. Chem., 63, 3346 (1998).
14. C. M. Suter, J. P. McKenzie and C. E. Maxwell, J. Am. Chem. Soc., 58, 717 (1936).
15. E. Schemitz, Chem. Ber., 6, 1133 (1958).
16. D. Seebach, J. J. Lohmann, M. A. Syfrig and M. Yoshifuji, Tetrahedron, 39, 1963 (1983).
17. M. P. Isabelle and D. Seebach, Helv. Chim. Acta, 70, 1944 (1987).
18. L. I. Zakharkin, D. N. Maslin and V. V. Gavrilenko, Tetrahedron, 25, 5555 (1969).
19. A. I. Meyers, Aldrichimica Acta, 18, 59 (1985).
20. See also ref. 12 and D. L. Comins and M. M. Badawi, Heterocycles, 32, 1869 (1991);
21. D. Seebach, I. M. P. Hubwe and M. Syfrig, Helv. Chim. Acta, 70, 1357 (1987);
22. M. D.Rozwadowska, Heterocycles, 39, 903 (1994).
23. R.G. R. Bacon and O. J. Stewart, J. Chem. Soc., 4953 (1965).
24. J.-F. Marcoux, S. Doye and S. L. Buchwald, J. Am. Chem. Soc., 119, 10539 (1997).
25. M. Tomita, Yakugaku Zasshi, 58, 510 (1938).
26. G. Wagner and M. Feigel, Tetrahedron, 49, 10831 (1993).
27. R. L. Hillard, C. A. Parnell and K. P. C. Vollhardt, Tetrahedron, 39, 905 (1983).
28. M. Yoshifuji and D. Seebach, Heterocycles, 19, 161 (1982).
29. A. P. Venkov and L. K. Lukanov, Synthesis, 1, 59 (1989).
30. A. P. Venkov and S. M. Statkova-Abeghe, Synth. Commun., 25, 1817 (1995).
31. Coutts, I.G.C., Hadfield, J.A. and Huddleston, P.R., J.Chem.Res., 9, 2412 (1981).