Synthesis of 3-hydroxy-5-oxonene via 2,3-epoxy-5-oxonene

Chemistry Letters

Volumn , Issue 7, 1997, Pages 665-666

  Fujiwara, Kenshu ^a   Tsunashima, Misa ^a   Awakura, Daisuke ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031492478     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.665     Document Type: Article

References (39)

1. K. Kurata, A. Furusaki, K. Suchiro, C. Katayama, and T. Suzuki, Chem. Lett., 1982, 1031.
2. M. Suzuki, E. Kurosawa, A. Furusaki, S. Katsuragi, and T. Matsumoto, Chem. Lett., 1984, 1033.
3. a) T. J. King, S. Imre, A. Öztunc, and R. H. Thomson, Tetrahedron Lett., 1453 (1979);
4. b) B. M. Howard, G. R. Schulte, W. Fenical, B. Solheim, and J. Clardy, Tetrahedron , 36, 1747 (1980);
5. c) Y. Gopichand, F. J. Shumitz, J. Shelly, A. Rahman, and D. van der Helm, J. Org. Chem., 46, 5192 (1981);
6. d) M. Norte, A. G. González, F. Cataldo, M. L. Rodríguez, and I. Brito, Tetrahedron ,47, 9411 (1991).
7. a) L. E. Overman, T. A. Blumenkopf, A. Castañeda, and A. S. Thompson, J. Am. Chem. Soc., 108, 3516 (1986);
8. b) K. C. Nicolaou, C. V. C. Prasad, C.-K. Hwang, M. E. Duggan, and C. A. Veale, J. Am. Chem. Soc., 111, 5321 (1989);
9. c) K. C. Nicolaou, C. V. C. Prasad, and W. W. Ogilvie, J. Am. Chem. Soc., 112, 4988 (1990);
10. d) K. C. Nicolaou, D. G. McGarry, P. K. Somers, B. H. Kim, W. W. Ogilvie, G. Yiannikouros, C. V. C. Prasad, C. A. Veale, and R. R. Hark, J. Am. Chem. Soc., 112, 6263 (1990);
11. e) N. R. Curtis, A. B. Holmes, and M. G. Loony, Tetrahedron Lett., 33, 671 (1992);
12. f) N. R. Curtis and A. B. Holmes, TetrahedronLett.,33,675(1992);
13. g) R. W. Carling, J. S. Clark, and A. B. Holmes, J. Chem. Soc. Perkin Trans. 1 1992, 83;
14. h) M. Isobe, C. Yenjai, and S. Tanaka, Synlett, 1994, 916;
15. i) A. Brandes and H.M.R. Hoffmann, Tetrahedron,51,145(1995);
16. j) K. Fujiwara, M. Tsunashima, D. Awakura, and A. Murai, Tetrahedron Lett., 36, 8263 (1995);
17. k) M. Isobe, S. Hosokawa, and K. Kira, Chem. Lett., 1996, 473;
18. l) E. Alvarez, M. Delgado, M. T. Díaz, L. Hanxing, R. Péres, and J. D. Martín, Tetrahedron Lett., 37, 2865 (1996);
19. m) T. Oishi, M. Shoji, K. Maeda, N. Kumahara, and M. Hirama, Synlett, 1996, 1165;
20. n) J. S. Clark and J. G. Kettle, Tetrahedron Lett., 38, 127 (1997);
21. o) M. Inoue, M. Sasaki, and K. Tachibana, Tetrahedron Lett., 38, 1611 (1997).
22. 4c
23. a) R. W. Murray and R. Jeyaraman, J. Org. Chem., 50, 2847 (1985);
24. b) W. Adam, Y.-Y. Chan, D. Cremer, J. Gauss, D. Schcutzow,and M. Schindler, J. Org.Chem.,52,2800(1987);
25. c) Dimethyldioxirane-acetonesolutionprepared according to Adam's method was dried with molecular sieves 4 Å before use.
26. 2O, reflux, then 14, 97%;
27. 2,20°C, 1.5 h, 97%;
28. c)BuLi (1 eq), THF, -20°C, 10min, then 16 (0.5eq), THF-HMPA (5:1), -20°C, 2h, then 20°C, 2 h, 73% (from 16), 45% recovery of 15;
29. 2, quinoline-EtOH(1:250), 20°C, 1 h, 98%;
30. e) 2MHCl-THF(1:1), 20°C, 5 h;
31. 2O (3.5:1), 0°C, 1 h, 87% (2 steps);
32. 3, reflux, 2 days, 72%;
33. 2S, -78°C, 10 min, then -40°C, 16 h, 82%.
34. Thereactivityof 2-methyl-2-butene with dimethyldioxirane was comparable as that of the enol ether part of 3 at -40°C.
35. 3, 23°C) for epoxides 4 and 5. Epoxide 4: δ 0.91 (3H, t, J=7 Hz, H2″ or 2′), 1.01 (3H, t, J=7 Hz, H2″ or 2″), 2.50 (1H, td, J=5, 13 Hz, H4a), 2.57-2.67 (1H, m, H4b), 2.92 (1H, dd, J=5, 9 Hz, H3), 3.56 (1H, tdd, J=4, 7, 10 Hz, H9), 5.60-5.68 (2H, m, H5 and 6); Epoxide 5: δ 0.86 (3H, t, J=8 Hz, H2′ or 2″), 0.93 (3H, t, J=8 Hz, H2″ or 2′), 2.35 (1H, brtd. J=7, 13 Hz, H4a), 2.83-2.90 (1H, J=2, 7, 13 Hz, H4b), 3.02 (1H, dd, J=2, 7 Hz, H3), 3.89 (1H, brtdd, J=4, 7, 12 Hz, H9), 5.44-5.54 (2H, m, H5 and 6).
36. 2O after stirring for 2 hours at 20°C.
37. 4 to give 9. We wish to describe the rearrangement in detail elsewhere. For aluminum reagent catalyzed rearrangement of epoxide, see: K. Maruoka, S. Nagahara, T. Ooi, and H. Yamamoto, Tetrahedron Lett., 30, 5607 (1989). equation presented
38. 4g
39. 4m