Preparation of tetrahydrofuran, γ-lactone, chromanol and pyrrolidine systems by sequential 5-exo-digonal radical cyclization, 1,5-hydrogen transfer from silicon, and 5-endo-trigonal cyclization

Chemical Communications

Volumn , Issue 14, 1996, Pages 1605-1606

  Clive, Derrick L J ^a   Yang, Wen ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002004316     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001605     Document Type: Article

References (30)

1. D. L. J. Clive and M. Cantin, J. Chem. Soc., Chem. Commun., 1995, 319.
2. (a) G. D. Mendenhall, J. D. Protasiewicz, C. E. Brown, K. U. Ingold and J. Lusztyk, J. Am. Chem. Soc., 1994, 116, 1718;
3. (b) See ref. 1 and references cited therein.
4. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734; A. L. J. Beckwith, C. J. Easton and A. K. Serelis, J. Chem. Soc., 1980, 482.
5. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734; A. L. J. Beckwith, C. J. Easton and A. K. Serelis, J. Chem. Soc., 1980, 482.
6. A. Martinez-Grau and D. P. Curran, J. Org. Chem., 1995, 60, 8332.
7. M. Farines and J. Soulier, Bull. Soc., Chim. Fr., 1970, 332.
8. (a) P. Dowd and P. Kennedy, Synth. Commun., 1981, 11, 935;
9. (b) R. M. Scarborough Jr. and A. B. Smith III, Tetrahedron Lett., 1977, 4361;
10. (c) D. Liotta and H. Santiestaban, Tetrahedron Lett., 1977, 4369;
11. (d) S. V. Ley, I. A. O'Neil and C. M. R. Low, Tetrahedron, 1986, 42, 5363.
12. Cf. M. Hirama, I. Nishizaki, T. Shigemoto and S. Itô, J. Chem. Soc., Chem. Commun., 1986, 393.
13. T. W. Hart, D. A. Metcalfe and F. Scheinmann, J. Chem. Soc., Chem. Commun., 1979, 156.
14. M. W. Walter, R. M. Adlington, J. E. Baldwin, J. Chuhan and C. J. Schofield, Tetrahedron Lett. 1995, 36, 7761.
15. M. Koreeda and J. Wu, Synlett, 1995, 850 and references cited therein.
16. M. Gomis, B. S. Kirkiachurian, J. Likforman and J. Mahuteau, Bull. Chem. Soc. Fr., 1988, 585.
17. A. L. J. Beckwith and S. A. Glover, Aust. J. Chem., 1987, 40, 157.
18. A. L. J. Beckwith and G. Moad, J. Chem. Soc., Chem. Commun., 1974, 472.
19. Cf. (a) G. Stork, R. Mook Jr., S. A. Biller and S. D. Rychnovsky, J. Am. Chem. Soc., 1983, 105, 3741. (b) W. R. Leonard and T. Livinghouse, Tetrahedron Lett., 1985, 26, 6431; (c) L. D. M. Lolkema, H. Hiemstra, A. Ayachi Al Ghouch and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 1491; (d) A. J. Clark, K. Jones, C. McCarthy and J. M. D. Storey, Tetrahedron Lett., 1991, 32, 2829; (e) T. Honda, M. Satoh and Y. Kobayashi, J. Chem. Soc., Perkin Trans 1, 1992, 1557; (f) See also refs. 1 and 4.
20. Cf. (a) G. Stork, R. Mook Jr., S. A. Biller and S. D. Rychnovsky, J. Am. Chem. Soc., 1983, 105, 3741. (b) W. R. Leonard and T. Livinghouse, Tetrahedron Lett., 1985, 26, 6431; (c) L. D. M. Lolkema, H. Hiemstra, A. Ayachi Al Ghouch and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 1491; (d) A. J. Clark, K. Jones, C. McCarthy and J. M. D. Storey, Tetrahedron Lett., 1991, 32, 2829; (e) T. Honda, M. Satoh and Y. Kobayashi, J. Chem. Soc., Perkin Trans 1, 1992, 1557; (f) See also refs. 1 and 4.
21. Cf. (a) G. Stork, R. Mook Jr., S. A. Biller and S. D. Rychnovsky, J. Am. Chem. Soc., 1983, 105, 3741. (b) W. R. Leonard and T. Livinghouse, Tetrahedron Lett., 1985, 26, 6431; (c) L. D. M. Lolkema, H. Hiemstra, A. Ayachi Al Ghouch and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 1491; (d) A. J. Clark, K. Jones, C. McCarthy and J. M. D. Storey, Tetrahedron Lett., 1991, 32, 2829; (e) T. Honda, M. Satoh and Y. Kobayashi, J. Chem. Soc., Perkin Trans 1, 1992, 1557; (f) See also refs. 1 and 4.
22. Cf. (a) G. Stork, R. Mook Jr., S. A. Biller and S. D. Rychnovsky, J. Am. Chem. Soc., 1983, 105, 3741. (b) W. R. Leonard and T. Livinghouse, Tetrahedron Lett., 1985, 26, 6431; (c) L. D. M. Lolkema, H. Hiemstra, A. Ayachi Al Ghouch and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 1491; (d) A. J. Clark, K. Jones, C. McCarthy and J. M. D. Storey, Tetrahedron Lett., 1991, 32, 2829; (e) T. Honda, M. Satoh and Y. Kobayashi, J. Chem. Soc., Perkin Trans 1, 1992, 1557; (f) See also refs. 1 and 4.
23. Cf. (a) G. Stork, R. Mook Jr., S. A. Biller and S. D. Rychnovsky, J. Am. Chem. Soc., 1983, 105, 3741. (b) W. R. Leonard and T. Livinghouse, Tetrahedron Lett., 1985, 26, 6431; (c) L. D. M. Lolkema, H. Hiemstra, A. Ayachi Al Ghouch and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 1491; (d) A. J. Clark, K. Jones, C. McCarthy and J. M. D. Storey, Tetrahedron Lett., 1991, 32, 2829; (e) T. Honda, M. Satoh and Y. Kobayashi, J. Chem. Soc., Perkin Trans 1, 1992, 1557; (f) See also refs. 1 and 4.
24. Cf. (a) G. Stork, R. Mook Jr., S. A. Biller and S. D. Rychnovsky, J. Am. Chem. Soc., 1983, 105, 3741. (b) W. R. Leonard and T. Livinghouse, Tetrahedron Lett., 1985, 26, 6431; (c) L. D. M. Lolkema, H. Hiemstra, A. Ayachi Al Ghouch and W. N. Speckamp, Tetrahedron Lett., 1991, 32, 1491; (d) A. J. Clark, K. Jones, C. McCarthy and J. M. D. Storey, Tetrahedron Lett., 1991, 32, 2829; (e) T. Honda, M. Satoh and Y. Kobayashi, J. Chem. Soc., Perkin Trans 1, 1992, 1557; (f) See also refs. 1 and 4.
25. (a) V. H. Rawal, S. P. Singh, C. Dufour and C. Michoud, J. Org. Chem., 1991, 56, 5245;
26. (b) Cf. S. D. Burke and J. Rancourt, J. Am. Chem. Soc., 1991, 113, 2335;
27. (c) Cf. M. D. Bachi, F. Frolow and C. Hoornaert, J. Org. Chem., 1983, 48, 1841.
28. C. Chen, D. Crich and A. Papadatos, J. Am. Chem. Soc., 1992, 114, 8313; M. D. Bachi and D. Denenmark, Heterocycles, 1989, 28, 583.
29. C. Chen, D. Crich and A. Papadatos, J. Am. Chem. Soc., 1992, 114, 8313; M. D. Bachi and D. Denenmark, Heterocycles, 1989, 28, 583.
30. A. Arnone, P. Bravo, M. Frigerio, F. Viani, G. Cavicchio and M. Crucianelli, J. Org. Chem., 1994, 59, 3459.