Total Synthesis of (±)-Tremulenolide A and (±)-Tremulenediol A via a Stereoselective Cyclopropanation/Cope Rearrangement Annulation Strategy

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 657-660

  Davies, Huw M L ^a   Doan, Brian D ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000353622     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971577a     Document Type: Article

References (22)

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2. Davies, H. M. L. Tetrahedron 1993, 49, 5203.
3. For recent synthetic studies of compounds related to the tremulanes, see: (a) Habeck, T.; Wolff, C.; Tochtermann, W. Tetrahedron Lett. 1995, 36, 2041. (b) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967.
4. For recent synthetic studies of compounds related to the tremulanes, see: (a) Habeck, T.; Wolff, C.; Tochtermann, W. Tetrahedron Lett. 1995, 36, 2041. (b) Davies, H. M. L.; Doan, B. D. Tetrahedron Lett. 1996, 37, 3967.
5. For examples of the use of the Cope rearrangement of divinylcyclopropanes for the synthesis of pseudoguaianes, see: (a) Marino, J. P.; Kaneko, T. J. Org. Chem. 1974, 39, 3175. (b) Marino, J. P.; Browne, L. J. Tetrahedron Lett. 1976, 3245. (c) Wender, P. A.; Eissenstat, M. A.; Filosa, M. P. J. Am. Chem. Soc. 1979, 101, 2196. (d) Wender, P. A.; Filosa, M. P. J. Org. Chem. 1976, 41, 3490. (e) Piers, E.; Nagakura, I. Tetrahedron Lett. 1976, 3237. (f) Piers, E.; Morton, H. E.; Nagakura, I.; Thies, R. W. Can. J. Chem. 1983, 61, 1226.
6. For examples of the use of the Cope rearrangement of divinylcyclopropanes for the synthesis of pseudoguaianes, see: (a) Marino, J. P.; Kaneko, T. J. Org. Chem. 1974, 39, 3175. (b) Marino, J. P.; Browne, L. J. Tetrahedron Lett. 1976, 3245. (c) Wender, P. A.; Eissenstat, M. A.; Filosa, M. P. J. Am. Chem. Soc. 1979, 101, 2196. (d) Wender, P. A.; Filosa, M. P. J. Org. Chem. 1976, 41, 3490. (e) Piers, E.; Nagakura, I. Tetrahedron Lett. 1976, 3237. (f) Piers, E.; Morton, H. E.; Nagakura, I.; Thies, R. W. Can. J. Chem. 1983, 61, 1226.
7. For examples of the use of the Cope rearrangement of divinylcyclopropanes for the synthesis of pseudoguaianes, see: (a) Marino, J. P.; Kaneko, T. J. Org. Chem. 1974, 39, 3175. (b) Marino, J. P.; Browne, L. J. Tetrahedron Lett. 1976, 3245. (c) Wender, P. A.; Eissenstat, M. A.; Filosa, M. P. J. Am. Chem. Soc. 1979, 101, 2196. (d) Wender, P. A.; Filosa, M. P. J. Org. Chem. 1976, 41, 3490. (e) Piers, E.; Nagakura, I. Tetrahedron Lett. 1976, 3237. (f) Piers, E.; Morton, H. E.; Nagakura, I.; Thies, R. W. Can. J. Chem. 1983, 61, 1226.
8. For examples of the use of the Cope rearrangement of divinylcyclopropanes for the synthesis of pseudoguaianes, see: (a) Marino, J. P.; Kaneko, T. J. Org. Chem. 1974, 39, 3175. (b) Marino, J. P.; Browne, L. J. Tetrahedron Lett. 1976, 3245. (c) Wender, P. A.; Eissenstat, M. A.; Filosa, M. P. J. Am. Chem. Soc. 1979, 101, 2196. (d) Wender, P. A.; Filosa, M. P. J. Org. Chem. 1976, 41, 3490. (e) Piers, E.; Nagakura, I. Tetrahedron Lett. 1976, 3237. (f) Piers, E.; Morton, H. E.; Nagakura, I.; Thies, R. W. Can. J. Chem. 1983, 61, 1226.
9. For examples of the use of the Cope rearrangement of divinylcyclopropanes for the synthesis of pseudoguaianes, see: (a) Marino, J. P.; Kaneko, T. J. Org. Chem. 1974, 39, 3175. (b) Marino, J. P.; Browne, L. J. Tetrahedron Lett. 1976, 3245. (c) Wender, P. A.; Eissenstat, M. A.; Filosa, M. P. J. Am. Chem. Soc. 1979, 101, 2196. (d) Wender, P. A.; Filosa, M. P. J. Org. Chem. 1976, 41, 3490. (e) Piers, E.; Nagakura, I. Tetrahedron Lett. 1976, 3237. (f) Piers, E.; Morton, H. E.; Nagakura, I.; Thies, R. W. Can. J. Chem. 1983, 61, 1226.
10. For examples of the use of the Cope rearrangement of divinylcyclopropanes for the synthesis of pseudoguaianes, see: (a) Marino, J. P.; Kaneko, T. J. Org. Chem. 1974, 39, 3175. (b) Marino, J. P.; Browne, L. J. Tetrahedron Lett. 1976, 3245. (c) Wender, P. A.; Eissenstat, M. A.; Filosa, M. P. J. Am. Chem. Soc. 1979, 101, 2196. (d) Wender, P. A.; Filosa, M. P. J. Org. Chem. 1976, 41, 3490. (e) Piers, E.; Nagakura, I. Tetrahedron Lett. 1976, 3237. (f) Piers, E.; Morton, H. E.; Nagakura, I.; Thies, R. W. Can. J. Chem. 1983, 61, 1226.
11. Hudlicky, T.; Fan, R.; Reed, J. W.; Gadamasetti, K. G. Org. React. 1992, 47, 2.
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13. Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 936.
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15. (a) Furber, M.; Herbert, J. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1989, 683.
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18. For examples of the effect of steric hindrance on the rate of the Cope rearrangement of divinylcyclopropanes, see: (a) Schneider, M. P.; Rau, A. J. Am. Chem. Soc. 1979, 101, 4426.
19. (b) Cantrell, W. R., Jr.; Davies, H. M. L. J. Org. Chem. 1991, 56, 723.
20. (a) Davies, H. M. L.; Peng, Z.-Q.; Houser, J. H. Tetrahedron Lett. 1994, 35, 8939.
21. (b) Davies, H, M, L.; Stafford, D. G.; Doan, B. D.; Houser, J. H. J. Am. Chem. Soc., submitted.
22. Davies, H. M. L.; Matasi. J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095.