Olefin metathesis in cyclic ether formation. Direct conversion of olefinic esters to cyclic enol ethers with Tebbe-type reagents

Journal of the American Chemical Society

Volumn 118, Issue 6, 1996, Pages 1565-1566

  Nicolaou, K C ^a,b   Postema, Maarten H D ^b   Claiborne, Christopher F ^b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

POLYETHER; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029920724     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9534866     Document Type: Article

References (26)

1. (a) Katz, T. J.; Lee, S. J.; Shippey, M. A. J. Mol. Catal. 1980, 8, 219.
2. (b) Howard, T. R.; Lee, J. B.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 6876.
3. For recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (c) Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon; New York, 1991; Vol. 5, Chapter 9.3.
4. For recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (c) Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon; New York, 1991; Vol. 5, Chapter 9.3.
5. For recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (c) Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon; New York, 1991; Vol. 5, Chapter 9.3.
6. (a) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855.
7. (b) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943.
8. (c) Martin, S. F.; Wagman, A. S. Tetrahedron Lett. 1995, 36, 1169.
9. (d) Kim, S.-H.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801.
10. For related work, see: (a) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800. (b) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029.
11. For related work, see: (a) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800. (b) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029.
12. (a) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
13. (b) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270.
14. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
15. For a related, but mechanistically different, closure, see: (a) Stille, J. R.; Santarsiero, B. D.; Grubbs, R. H. J. Org. Chem. 1990, 55, 843. (b) Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855.
16. For a related, but mechanistically different, closure, see: (a) Stille, J. R.; Santarsiero, B. D.; Grubbs, R. H. J. Org. Chem. 1990, 55, 843. (b) Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855.
17. Buffering the reaction with pyridine or 2,6-di-tert-butyl-4-methylpyridine did not stop this, presumably, Lewis-acid-catalyzed reaction.
18. Structure determination: (a) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golit, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (b) Lee, M. S.; Repeta, D. J.; Nakanishi, K.; Zagorski, M. G. J. Am. Chem. Soc. 1986, 108, 7855.
19. Structure determination: (a) Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golit, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773. (b) Lee, M. S.; Repeta, D. J.; Nakanishi, K.; Zagorski, M. G. J. Am. Chem. Soc. 1986, 108, 7855.
20. Total synthesis: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. (b) Nicolaou, K. C.; Ryjes, F. P. J. T.; Theodorakis, E. A.-. Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173.
21. Total synthesis: (a) Nicolaou, K. C.; Theodorakis, E. A.; Rutjes, F. P. J. T.; Tiebes, J.; Sato, M.; Untersteller, E.; Xiao, X.-Y. J. Am. Chem. Soc. 1995, 117, 1171. (b) Nicolaou, K. C.; Ryjes, F. P. J. T.; Theodorakis, E. A.-. Tiebes, J.; Sato, M.; Untersteller, E. J. Am. Chem. Soc. 1995, 117, 1173.
22. Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380.
23. (a) Staake, M.; lshida, S.; Yasumoto, T.; Murata, M.; Utsumi, H.; Hinomoto, T. J. Am. Chem. Soc. 1995, 117, 7019.
24. (b) Murata, M.; Naoki, H.; Matsunaga, S.; Satake, M., Yasumoto, T. J. Am. Chem Soc. 1994, 116, 7098.
25. For a palladium-catalyzed approach to maitotoxin-type fragments. see: Nicolaou, K. C.; Sato, M.; Miller, N. D.; Gunzner, J. L; Renaud, J.; Untersteller, E. Submitted for publication.
26. All new compounds exhibited satisfactory spectral and exact mass data. Yields refer to spectroscopically and chromatographically homogeneous materials.