A novel route to 2-fluoromethyl- and 2-hydroxymethyl-4-alkyl furans via allene oxides

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7437-7440

  Kabat, Marek M ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b HOFFMANN LA ROCHE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030574030     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01605-X     Document Type: Article

References (50)

1. 1. Comprehensive Heterocyclic Chemistry; Meth-Cohn, O., Ed.; Pergamon Press: New York, 1984; Vol 1.
2. 2. For general reviews of the chemistry of furans, see: a) Bosshard, P.; Eugster, C. H. In Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J., Eds; Academic Press: New York, 1966; Vol 7, pp 377-490.
3. b) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1982; Vol 30, pp 167-238.
4. c) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed; Academic Press: New York, 1982; Vol 31, pp 237-344.
5. d) Dean, F. M.; Sargent, M. V. In Comprehensive Heterocyclic Chemistry; Bird, C. W.; Cheeseman, G. W. H., Eds.; Pergamon Press: New York, 1984; Vol. 4, Part 3, pp 531-589.
6. e) Sargent, M. V.; Dean, F. M. In Comprehensive Heterocyclic Chemistry; Bird, C. W.; Cheeseman, G. W. H., Eds.; Pergamon Press, 1984; Vol. 4, Part 3, pp 599-659.
7. f) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Bird, C. W.; Cheeseman, G. W. H., Eds.; Pergamon Press: New York, 1984; Vol 4, Part 3, pp 657-712.
8. 3. a) Jung, J. H.; Lee, J. W.; Oh, D. Y. Tetrahedron Lett. 1995, 36, 923.
9. b) Kang, K.-T.; Sun U, J.; Hwang, S. S.; Jyung, K. K. Synth. Comm. 1994, 24, 2915.
10. c) Cormier, R. A.; Grosshans, C. A.; Skibbe, S. L. Synth. Comm. 1988, 18, 677.
11. d) Igarashi, S.; Haruta, Y.; Nishide, Y.; Kinoshita, H.; Inomata, K. Chem. Lett. 1989, 737.
12. e) Dean, F. M. Adv. Hetero. Chem. 1982, 31, 238.
13. f) Dean, F. M. Adv. Hetero. Chem. 1982, 30, 168.
14. g) Sargent, M. V.; Dean, F. M. Furans and their Benzo Derivatives: Reactivity, Synthesis and Applications. In Comp. Hetero. Chem. 1982, 3, 599.
15. h) Hegde, S. G.; Wolinsky, J. J. Org. Chem. 1982, 47, 3148.
16. 4. Grieco, P. A.; Pogonowski, C. S.; Burke, S. J. Org. Chem. 1975, 40, 542.
17. 5. a) Nieman, J. A.; Keay, B. A. Tetrahedron Lett. 1994, 35, 5335.
18. b) Lee, G. C. M.; Holmes, J. M.; Harcourt, D. A.; Garst, M. E. J. Org. Chem. 1992, 57, 3126.
19. c) Bock, I.; Bornowski, H.; Ranft, A.; Theis, H. Tetrahedron 1990, 46, 1199.
20. d) Obrecht, D.; Helv. Chim. Acta 1989, 72, 447.
21. e) Chiarello, J.; Joullie, M. M. Tetrahedron 1988, 44, 41.
22. f) Barnes, B. J.; Newcombe, P. J.; Norris, R. K.; Wilson, K. J. Chem. Soc., Chem. Commun. 1985, 1408.
23. g) Tanis, S. P.; Head, D. B. Tetrahedron Lett. 1984, 25, 4451.
24. h) Goldsmith, D.; Liotta, D.; Saindane, M.; Waykole, L.; Bowen, P. Tetrahedron Lett. 1983, 24, 5835.
25. i) Nolan, S. M.; Cohen, T. J. Org. Chem., 1981, 46, 2473.
26. j) Florentin, D.; Roques, B. P.; Fournie-Zaluski, M. C. Bull. Soc. Chim. Fr. 1976, 1999.
27. k) Fournie-Zaluski, M. C.; Chatain-Cathaud, C. Bull. Soc. Chim. Fr. 1974, 1571.
28. 6. a) Kabat, M. M. J. Org. Chem. 1995, 60, 1823.
29. b) Kabat, M. M. Tetrahedron Lett. 1993, 34, 8543.
30. c) Kabat, M. M. Tetrahedron: Asymm. 1993, 4, 1417.
31. d) Kabat, M. M. J. Fluorine Chem. 1989, 43, 435.
32. 7. Selected methods. a) Parson, J. G.; Rizzacasa, M. A. Tetrahedron Lett. 1994, 35, 8263.
33. b) Hon, Y.-S.; Chang, F. J.; Lu, L. J. Chem. Soc., Chem. Comm. 1994, 2041.
34. c) Matsuda, I.; Sakakibara, J.; Inoue, H.; Nagashima, H. Tetrahedron Lett. 1992, 39, 5799.
35. d) Campi, E.; Fitzmaurice, N. J.; Jackson, W. R.; Perlmutter, P.; Smallridge, A. J. Synthesis 1987, 1031.
36. e) Hayashi, M.; Mukayama, T. Chem. Lett. 1987, 1283.
37. f) Ochiai, M.; Fujita, E.; Arimoto, M.; Yamaguchi, H. Tetrahedron Lett. 1983, 24, 777.
38. g) Tius, M. A.; Astrab, D. P.; Gu, X. J. Org. Chem. 1987, 52, 2625.
39. 8. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
40. 4 reduction produced the 21-cyano-22-hydroxymethyl derivative which subsequently was acetylated then pyrolyzed to give the α,β-unsaturated nitrile according to ref. 9b. Reduction of this compound with Dibal-H followed by silylation of the 3-hydroxyl group afforded the unsaturated aldehyde 8. a) Patel, D. K.; Petrow, V.; Royer, R.; Stuart-Webb, I. A. J. Chem. Soc. 1952, 161.
41. b) Kurek, A.; Kabat, M. M.; Gumulka, M.; Wicha, J. Pol. J. Chem. 1981, 55, 1369.
42. 3 (M+) calcd 368.2351, found 368.2343.
43. 11. The biological activity of compounds 10, 11, 14, and 15 will be disclosed elsewhere.
44. 12. For review articles on allene oxides see: a) Smajda, W. Chem. Rev. 1983, 83, 263.
45. b) Chan, T. H.; Ong, B. S. Tetrahedron 1980, 36, 2289. See also:
46. c) Clemens, I. R.; Shipman, M.; Thorpe H. R. Synlett 1995, 1065.
47. d) Chan, T. H.; Ong, B. S. J. Org. Chem. 1978, 43, 2294.
48. 13. a) Brennan, M. B. C&E News 1996, February 19, 26.
49. b) Satyamurthy, N.; Namavari, M.; Barrio, J. B. Chemtech 1994, March, 25.
50. c) Dagani, R. C&E News 1981, Nov. 9, 30.