Synthesis of alkenyl-substituted cyclic enol ethers by catalytic ring-closing metathesis of alkynyl ethers

Chemical Communications

Volumn , Issue 23, 1998, Pages 2629-2630

  Stephen Clark, J ^a   Trevitt, Graham P ^a   Boyall, Dean ^a   Stammen, Blanda ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; ALKYNYL GROUP; ETHER DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS;

EID: 0032495041     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a807667g     Document Type: Article

References (27)

1. For a review of marine polycyclic ether toxins, see T. Yasumoto and M. Murata, Chem. Rev., 1993, 93, 1897.
2. For recent syntheses of brevetoxins A and B, see K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1996, 35, 589;
3. K. C. Nicolaou, Z. Yang, G.-Q. Shi, J. L. Gunzner, K. A. Agrios and P. Gärtner, Nature, 1998, 392, 264.
4. M. Satake, M. Murata and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 361.
5. (a) J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 123;
6. (b) J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 127.
7. K. C. Nicolaou, M. H. D. Postema and C. F. Claiborne, J. Am. Chem. Soc., 1996, 118, 1565;
8. T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 980;
9. M. Delgado and J. D. Martin, Tetrahedron Lett., 1997, 38, 6299;
10. M. T. Crimmins and A. L. Choy, J. Org. Chem., 1997, 62, 7548.
11. For recent reviews concerning ring-closing metathesis, see R. H. Grubbs, S. J. Miller and G. C. Fu, Acc. Chem. Res. 1995, 28, 446;
12. H.-G. Schmalz, Angew. Chem., Int. Ed. Engl., 1995, 34, 1833;
13. M. Schuster and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 2036;
14. S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371;
15. R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413.
16. N. Chatani, T. Morimoto, T. Muto and S. Murai, J. Am. Chem. Soc., 1994, 116, 6049.
17. (a) A. Kinoshita and M. Mori, Synlett, 1994, 1020;
18. (b) A. Kinoshita and M. Mori, J. Org. Chem., 1996, 61, 8356;
19. (c) A. Kinoshita and M. Mori, Heterocycles, 1997, 46, 287.
20. A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson and P. A. Procopiou, Chem. Commun., 1997, 1375.
21. For the functionalisation of a closely related system by this procedure, see E. Alvarez, M. Rico, R. M. Rodríguez, D. Zurita and J. D. Martín, Tetrahedron Lett., 1992, 33, 3385.
22. E. W. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981, ch. 12, pp. 142-164.
23. P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1995, 34, 2039.
24. J. Mulzer and A. Angermann, Tetrahedron Lett., 1983, 24, 2843;
25. J. Jurczak, S. Pikul and T. Bauer, Tetrahedron, 1986, 42, 447.
26. A. Moyano, F. Charbonnier and A. E. Greene, J. Org. Chem., 1987, 52, 2919.
27. O. Fujimura, G. C. Fu and R. H. Grubbs, J. Org. Chem., 1994, 59, 4029.