Tungsten carbonyl-induced cyclizations of alkynyl alcohols to dihydropyranylidene carbenes and α-stannyl dihydropyrans

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4675-4678

  McDonald, Frank E ^a   Bowman, Jason L ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; TUNGSTEN;

ARTICLE; DRUG SYNTHESIS;

EID: 0030183224     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00961-6     Document Type: Article

References (44)

1. 1. (a) Chisholm, M. H.; Clark, H. C. J. Am. Chem. Soc. 1972, 94, 1532.
2. (b) Chisholm, M. H.; Clark, H. C. Acc. Chem. Res. 1973, 6, 241.
3. 2. (a) Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 47, C17.
4. (b) Oguro, K.; Wada, M.; Okawara, R. J. Organomet. Chem. 1978, 159, 417.
5. (c) Bruce, M. I.; Swincer, A. G.; Thomson, B. J.; Wallis, R. C. Aust. J. Chem. 1980, 33, 2605.
6. (d) Marten, D. F. J. Chem. Soc., Chem. Commun. 1980, 341.
7. (e) Curtis, P. J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1984, 747.
8. (f) Parlier, A.; Rudler, H. J. Chem. Soc., Chem. Commun. 1986, 514.
9. (g) Dötz, K. H.; Sturm, W.; Alt, H. G. Organometallics 1987, 6, 1424.
10. (h) Hoover, J. F.; Stryker, J. M. J. Am. Chem. Soc. 1990, 112, 464.
11. (i) O'Connor, J. M.; Pu, L.; Rheingold, A. L. J. Am. Chem. Soc. 1990, 112, 6232.
12. (j) Le Bozec, H.; Ouzzine, K.; Dixneuf, P. H. Organometallics 1991, 10, 2768.
13. (k) Werner, H.; Knaup, W.; Schulz, M. Chem. Ber. 1991, 124, 1121.
14. (l) Stang, P. J.; Huang, Y. H. J. Organomet. Chem. 1992, 431, 247.
15. (m) Hinkle, R. J.; Stang, P. J.; Arif, A. M. Organometallics 1993, 12, 3510.
16. (n) Quayle, P.; Rahman, S.; Ward, E. L. M.; Herbert, J. Tetrahedron Lett. 1994, 35, 3801.
17. (o) Ruiz, N.; Peron, D.; Dixneuf, P. H. Organometallics 1995, 14, 1095.
18. (p) Schmidt, B.; Kocienski, P.; Reid, G. Tetrahedron 1996, 52, 1617.
19. 3. For recent applications of this concept to the synthesis of γ-butyrolactone natural products via the group VI metal carbenes 2 (n = 0, M = Cr, W), see: (a) Quayle, P.; Ward, E. L. M.; Taylor, P. Tetrahedron Lett. 1994, 35, 8883.
20. (b) Quayle, P.; Rahman, S.; Herbert, J. Tetrahedron Lett. 1995, 36, 8087.
21. 4. (a) McDonald, F. E.; Connolly, C. B.; Gleason, M. M.; Towne, T. B.; Treiber, K. D. J. Org. Chem. 1993, 58, 6952.
22. (b) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363.
23. (c) McDonald, F. E.; Gleason, M. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 350.
24. 5. McDonald, F. E.; Schultz, C. C.; Chatterjee, A. K. Organometallics 1995, 14, 3628.
25. 5, n = 1) from 4-pentyn-1-ol has been reported with chromium pentacarbonyl - ether complex (ref. 2g), but this procedure requires low temperature photolysis of chromium hexacarbonyl in ether solvent in the presence of alkynol substrate, and in our hands has not proven reproducible for synthesis of six-membered ring oxacarbenes.
26. 7. Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154.
27. 8. Six-membered ring oxacarbenes of group VI metals can also be formed by radical (ref. 8a) or anionic (ref. 8b) additions to α,β-unsaturated metal oxacarbenes. (a) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 9855.
28. (b) Aoki, S.; Fujimura, T.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 2985.
29. 9. (a) Compound 6: Magnus, P.; Slater, M. J.; Principe, L. M. J. Org. Chem. 1989, 54, 5148.
30. (b) Compounds 7 and 8 were prepared from 1-hexyn-5-one (Sammes, P. G.; Greenberg, S. G.; Davies, L. B. J. Chem. Soc., Perkin Trans. I 1981, 1909) by lithium aluminum hydride reduction (7, 67% yield) or methylmagnesium bromide addition (8, 50%).
31. 2, 0°C (11% yield, four steps).
32. 9) 369.1184, found 369.1164.
33. 8-THF) indicate that organic products such as the corresponding lactones (arising from oxidation) or cyclic enol ethers (from base-induced demetallation) are not formed.
34. 12. For representative synthesis applications of α-stannyl dihydropyrans, see: (a) Hanessian, S.; Martin, M.; Desai. R. C. J. Chem. Soc., Chem. Commun. 1986, 926.
35. (b) Lesimple, P.; Beau, J.-M.; Jaurand, G.; Sinaÿ, P. Tetrahedron Lett. 1986, 27, 6201.
36. (c) Paquette, L. A.; Oplinger, J. A. Tetrahedron 1989, 45, 107.
37. (d) Friesen, R. W.; Sturino, C. F. J. Org. Chem. 1990, 55, 5808.
38. (e) MacLeod, D.; Moorcroft, D.; Quayle, P.; Dorrity, M. R. J.; Malone, J. F.; Davies, G. M. Tetrahedron Lett. 1990, 31, 6077.
39. (f) Boeckman, R. K.; Charette, A. B.; Asberom, T.; Johnston, B. H. J. Am. Chem. Soc. 1991, 113, 5337.
40. (g) Grondin, R.; Leblanc, Y.; Hoogsteen, K. Tetrahedron Lett. 1991, 32, 5021.
41. (h) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 223, 157.
42. (i) Lesimple, P.; Beau, J.-M. Bioorg. Med. Chem. 1994, 2, 1319.
43. (j) Bearder, J. R.; Dewis, M. L.; Whiting, D. A. J. Chem. Soc., Perkin Trans. I 1995, 227.
44. (k) Ashworth, P.; Broadbelt, B.; Jankowski, P.; Kocienski, P.; Pimm, A.; Bell, R. Synthesis 1995, 199.