Synthesis of alkenyl-substituted cyclic enol ethers by catalytic ring-closing metathesis of alkynyl ethers
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J. Stephen Clark, Graham P. Trevitt, Dean Boyall and Blanda Stammen
Abstract
Ring-closing enyne metathesis can be used to prepare alkenyl-substituted six- and seven-membered cyclic enol ethers in moderate to good yield.
References
For a review of marine polycyclic ether toxins, see T. Yasumoto and M. Murata, Chem. Rev., 1993, 93, 1897 Search PubMed.
For recent syntheses of brevetoxins A and B, see K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1996, 35, 589 Search PubMed; K. C. Nicolaou, Z. Yang, G.-Q. Shi, J. L. Gunzner, K. A. Agrios and P. Gärtner, Nature, 1998, 392, 264 CAS.
M. Satake, M. Murata and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 361 CrossRefCAS.
(a) J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 123 CrossRefCAS;
(b) J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 127 CrossRef.
K. C. Nicolaou, M. H. D. Postema and C. F. Claiborne, J. Am. Chem. Soc., 1996, 118, 1565 CrossRefCAS; T. Oishi, Y. Nagumo and M. Hirama, Synlett, 1997, 980 CAS; M. Delgado and J. D. Martín, Tetrahedron Lett., 1997, 38, 6299 CrossRefCAS; M. T. Crimmins and A. L. Choy, J. Org. Chem., 1997, 62, 7548 CrossRefCAS.
For recent reviews concerning ring-closing metathesis, see R. H. Grubbs, S. J. Miller and G. C. Fu, Acc. Chem. Res., 1995, 28, 446 Search PubMed; H.-G. Schmalz, Angew. Chem., Int. Ed. Engl., 1995, 34, 1833 CrossRefCAS; M. Schuster and S. Blechert, Angew. Chem., Int. Ed. Engl., 1997, 36, 2036 CrossRefCAS; S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371 CrossRef; R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413 RSC.
N. Chatani, T. Morimoto, T. Muto and S. Murai, J. Am. Chem. Soc., 1994, 116, 6049 CrossRefCAS.
(a) A. Kinoshita and M. Mori, Synlett, 1994, 1020 CrossRefCAS;
(b) A. Kinoshita and M. Mori, J. Org. Chem., 1996, 61, 8356 CrossRefCAS;
(c) A. Kinoshita and M. Mori, Heterocycles, 1997, 46, 287 CAS.
A. G. M. Barrett, S. P. D. Baugh, D. C. Braddock, K. Flack, V. C. Gibson and P. A. Procopiou, Chem. Commun., 1997, 1375 RSC.
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 Search PubMed.
E. W. Colvin,
Silicon in Organic Synthesis,
Butterworths,
London,
1981, ch. 12,
pp. 142–164 Search PubMed.
P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1995, 34, 2039 CrossRefCAS.
J. Mulzer and A. Angermann, Tetrahedron Lett., 1983, 24, 2843 CrossRefCAS; J. Jurczak, S. Pikul and T. Bauer, Tetrahedron, 1986, 42, 447 CrossRefCAS.
A. Moyano, F. Charbonnier and A. E. Greene, J. Org. Chem., 1987, 52, 2919 CrossRefCAS.
O. Fujimura, G. C. Fu and R. H. Grubbs, J. Org. Chem., 1994, 59, 4029 CrossRefCAS.
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