Organozirconium methods for the efficient construction of the bicyclo[9.3.0]tetradecane dolabellane skeleton

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7661-7664

  Luker, Tim ^a   Whitby, Richard J ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CYCLOPENTANE DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030583468     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01707-8     Document Type: Article

References (41)

1. 1. Ireland, C.; Faulkner, D. J.; Finer, J.; Clardy, J. J. Am. Chem. Soc. 1976, 98, 4664.
2. 2. a) Matsuo, A.; Uohama, K.; Hayashi, S.; Connolly, J. D. Chem. Lett. 1984, 599. Revised structure:
3. b) Matsuo, A.; Yoshida, K.; Uohama, K.; Hayashi, S.; Connolly, J. D.; Sim, G. A. Chem. Lett. 1985, 935.
4. c) Matsuo, A.; Yoshida, K.; Fukazawa, Y.; Nakayama, M.; Kuriyama, K. Chem. Lett. 1987, 369.
5. 3. Mori, K.; Iguchi, K.; Yamada, N.; Yamada, Y.; Inouye, Y. Tetrahedron Lett. 1987, 28, 5673.
6. 4. Rao, C. B.; Pullaiah, K. C.; Surapaneni, R. K.; Sullivan, B. W.; Albizati, K. F.; Faulkner, D. J.; Cunheng, H.; Clardy, J. J. Org. Chem. 1986, 51, 2736.
7. 5. Bowden, B. F.; Braekman, J. -C.; Coll, J. C.; Mitchell, S. J. Aus. J. Chem. 1980, 33, 927. Jenny, L.; Borschberg, H-J.; Acklin, P. Tetrahedron 1996, 52, 1549.
8. 5. Bowden, B. F.; Braekman, J. -C.; Coll, J. C.; Mitchell, S. J. Aus. J. Chem. 1980, 33, 927. Jenny, L.; Borschberg, H-J.; Acklin, P. Tetrahedron 1996, 52, 1549.
9. 6. Corey, E.J.; Kania, R.S. J. Am. Chem. Soc. 1996, 118, 1229 (dolabellatrienone). Jenny, L.; Borschberg, H-J. Helv. Chim. Acta. 1995, 78, 715 (δ-araneosene). Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 35 (neodolabellenol). For earlier synthesis of the bicyclo[9.3.0] skeleton: Williams, D. R.; Coleman, P. J.; Nevill, C. R.; Robinson, L. A. Tetrahedron Lett. 1993, 34, 7895. Mehta, G.; Karra, S. R.; Krishnamurthy, N. Tetrahedron Lett. 1994, 35, 2761. Williams, D.R.; Coleman, P.J.; Henry, S.S. J. Am. Chem. Soc. 1993, 775, 11654.
10. 6. Corey, E.J.; Kania, R.S. J. Am. Chem. Soc. 1996, 118, 1229 (dolabellatrienone). Jenny, L.; Borschberg, H-J. Helv. Chim. Acta. 1995, 78, 715 (δ-araneosene). Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 35 (neodolabellenol). For earlier synthesis of the bicyclo[9.3.0] skeleton: Williams, D. R.; Coleman, P. J.; Nevill, C. R.; Robinson, L. A. Tetrahedron Lett. 1993, 34, 7895. Mehta, G.; Karra, S. R.; Krishnamurthy, N. Tetrahedron Lett. 1994, 35, 2761. Williams, D.R.; Coleman, P.J.; Henry, S.S. J. Am. Chem. Soc. 1993, 775, 11654.
11. 6. Corey, E.J.; Kania, R.S. J. Am. Chem. Soc. 1996, 118, 1229 (dolabellatrienone). Jenny, L.; Borschberg, H-J. Helv. Chim. Acta. 1995, 78, 715 (δ-araneosene). Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 35 (neodolabellenol). For earlier synthesis of the bicyclo[9.3.0] skeleton: Williams, D. R.; Coleman, P. J.; Nevill, C. R.; Robinson, L. A. Tetrahedron Lett. 1993, 34, 7895. Mehta, G.; Karra, S. R.; Krishnamurthy, N. Tetrahedron Lett. 1994, 35, 2761. Williams, D.R.; Coleman, P.J.; Henry, S.S. J. Am. Chem. Soc. 1993, 775, 11654.
12. 6. Corey, E.J.; Kania, R.S. J. Am. Chem. Soc. 1996, 118, 1229 (dolabellatrienone). Jenny, L.; Borschberg, H-J. Helv. Chim. Acta. 1995, 78, 715 (δ-araneosene). Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 35 (neodolabellenol). For earlier synthesis of the bicyclo[9.3.0] skeleton: Williams, D. R.; Coleman, P. J.; Nevill, C. R.; Robinson, L. A. Tetrahedron Lett. 1993, 34, 7895. Mehta, G.; Karra, S. R.; Krishnamurthy, N. Tetrahedron Lett. 1994, 35, 2761. Williams, D.R.; Coleman, P.J.; Henry, S.S. J. Am. Chem. Soc. 1993, 775, 11654.
13. 6. Corey, E.J.; Kania, R.S. J. Am. Chem. Soc. 1996, 118, 1229 (dolabellatrienone). Jenny, L.; Borschberg, H-J. Helv. Chim. Acta. 1995, 78, 715 (δ-araneosene). Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 35 (neodolabellenol). For earlier synthesis of the bicyclo[9.3.0] skeleton: Williams, D. R.; Coleman, P. J.; Nevill, C. R.; Robinson, L. A. Tetrahedron Lett. 1993, 34, 7895. Mehta, G.; Karra, S. R.; Krishnamurthy, N. Tetrahedron Lett. 1994, 35, 2761. Williams, D.R.; Coleman, P.J.; Henry, S.S. J. Am. Chem. Soc. 1993, 775, 11654.
14. 6. Corey, E.J.; Kania, R.S. J. Am. Chem. Soc. 1996, 118, 1229 (dolabellatrienone). Jenny, L.; Borschberg, H-J. Helv. Chim. Acta. 1995, 78, 715 (δ-araneosene). Williams, D. R.; Coleman, P. J. Tetrahedron Lett. 1995, 36, 35 (neodolabellenol). For earlier synthesis of the bicyclo[9.3.0] skeleton: Williams, D. R.; Coleman, P. J.; Nevill, C. R.; Robinson, L. A. Tetrahedron Lett. 1993, 34, 7895. Mehta, G.; Karra, S. R.; Krishnamurthy, N. Tetrahedron Lett. 1994, 35, 2761. Williams, D.R.; Coleman, P.J.; Henry, S.S. J. Am. Chem. Soc. 1993, 775, 11654.
15. 7. a) Luker, T.; Whitby, R. J. Tetrahedron Lett. 1994, 35, 785.
16. b) Luker, T.; Whitby, R. J. Tetrahedron Lett. 1994, 35, 9465.
17. c) Luker, T.; Whitby, R. J. Tetrahedron Lett. 1995, 36, 4109.
18. d) Gordon, G. J.; Whitby, R. J. Synlett 1995, 77.
19. 8. Rousset, C. J.; Swanson, D. R.; Lamaty, F.; Negishi, E. Tetrahedron Lett. 1989, 30, 5105. Nugent, W. A.; Taber, D. F. J. Am. Chem. Soc. 1989, 111, 6435.
20. 8. Rousset, C. J.; Swanson, D. R.; Lamaty, F.; Negishi, E. Tetrahedron Lett. 1989, 30, 5105. Nugent, W. A.; Taber, D. F. J. Am. Chem. Soc. 1989, 111, 6435.
21. 9. Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 48, 5041. Corey, E. J.; Kirst, H. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1970, 92, 6314.
22. 9. Corey, E. J.; Kirst, H. A. Tetrahedron Lett. 1968, 48, 5041. Corey, E. J.; Kirst, H. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1970, 92, 6314.
23. 13C NMR, IR, MS and either HRMS or elemental analysis.
24. 11. a) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281.
25. b) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585.
26. c) Cintas, P. Synthesis 1992, 248.
27. 2 suspension before reaction greatly improved the yield and reproducability.
28. 12. a) Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. H. J. Am. Chem. Soc. 1967, 89, 4245.
29. b) Corey, E. J.; Katzenellenbogen, J. A.; Gilman, N. W.; Roman, S. A.; Erickson, B. W. J. Am. Chem. Soc. 1968, 90, 5618.
30. c) Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 47, 4595.
31. 12.d) Marshall, J. A.; Jenson, T. M.; DeHoff, B. S. J. Org. Chem. 1987, 52, 3860.
32. 12.e) Marshall, J. A.; Lebreton, J.; DeHoff, B. S.; Jenson, T. M. J. Org. Chem. 1987, 52, 3883.
33. 13. Corey, E. J.; Posner, G. H. J. Am. Chem. Soc. 1967, 89, 3911.
34. 6: 4.64 (1H, td, J = 10.3, 5.0 Hz), with that observed for 6β, 12β-dihydroxy-3E, 7E-dolabelladiene (ref 2b): 4.62 (1H, td, J = 10.0, 5.0 Hz).
35. 15. For t-hexyldimethylsilyl-protected analogue: Solladie, G.; Berl, V. Synlett 1991, 795.
36. 16. Corey, E. J.; Pyne, S. G.; Su, W. Tetrahedron Lett. 1983, 24, 4883.
37. 17. a) Takayanagi, H.; Uyehara, T.; Kato, T. J. Chem. Soc., Chem. Commun. 1978, 359.
38. b) Marshall, J. A.; Cleary, D. G. J. Org. Chem. 1986, 57, 858.
39. c) Takeda, K.; Urahata, M.; Yoshii, E. J. Org. Chem. 1986, 51, 4737.
40. d) Crich, D.; Natarajan, S. J. Chem. Soc., Chem. Commun. 1995, 85.
41. 18. Brown, A. C.; Carpino, L. A. J. Org. Chem. 1985, 50, 1749.