Synthesis of the Spatane Nucleus (cis-anti-cis-tricyclo[5.3.0.02,6]decane) using the Pauson-Khand Reaction with a Remarkable Reversal in Regioselectivity

Journal of Organic Chemistry

Volumn 63, Issue 5, 1998, Pages 1379-1389

  Kowalczyk, Bruce A ^a,b   Smith, Timothy C ^a,c   Dauben, William G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ROCHE BIOSCIENCE   (United States)

^c SOUTHWESTERN OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000030614     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9708194     Document Type: Article

References (33)

1. Reviews: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 233. (e) Schore, N. E. Chem. Rev. 1988, 88, 1081.
2. Reviews: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 233. (e) Schore, N. E. Chem. Rev. 1988, 88, 1081.
3. Reviews: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 233. (e) Schore, N. E. Chem. Rev. 1988, 88, 1081.
4. Reviews: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 233. (e) Schore, N. E. Chem. Rev. 1988, 88, 1081.
5. Reviews: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064. Pauson, P. L. Tetrahedron 1985, 41, 5855. Pauson, P. L. Organometallics in Organic Synthesis; de Meijere, A., tom Dieck, H., Eds.; Springer-Verlag: Berlin, 1987; p 233. (e) Schore, N. E. Chem. Rev. 1988, 88, 1081.
6. (a) Review: Salomon, R. G. Strategies and Tactics in Organic Synthesis; Academic Press, Inc.: New York, 1991; Vol. 3, p 381. Recent spatane synthesis work: (b) Murthi, K. K.; Salomon, R. G. Tetrahedron Lett. 1994, 35, 517. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1994, 35, 7031.
7. (a) Review: Salomon, R. G. Strategies and Tactics in Organic Synthesis; Academic Press, Inc.: New York, 1991; Vol. 3, p 381. Recent spatane synthesis work: (b) Murthi, K. K.; Salomon, R. G. Tetrahedron Lett. 1994, 35, 517. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1994, 35, 7031.
8. (a) Review: Salomon, R. G. Strategies and Tactics in Organic Synthesis; Academic Press, Inc.: New York, 1991; Vol. 3, p 381. Recent spatane synthesis work: (b) Murthi, K. K.; Salomon, R. G. Tetrahedron Lett. 1994, 35, 517. Miesch, M.; Cotte, A.; Franck-Neumann, M. Tetrahedron Lett. 1994, 35, 7031.
9. Dauben, W. G.; Kowalczyk, B. A. Tetrahedron Lett. 1990, 31, 635.
10. Scouten, C. G.; Barton, F. E.; Burgess, J. R.; Story, P. R.; Garst, J. F. J. Chem. Soc., Chem. Commun. 1969, 78.
11. Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233.
12. (a) Bladon, P.; Khand, I. U.; Pauson, P. L. J. Chem. Res. (S) 1977, 8.
13. (b) La Belle, B. E.; Knudsen, M. J.; Olmstead, M. M.; Hope, H.; Yanuck, M. D.; Schore, N. E. J. Org. Chem. 1985, 50, 5215.
14. Sampath, V.; Lund, E. C.; Knudsen, M. J.; Olmstead, M. M.; Schore, N. E. J. Org. Chem. 1987, 52, 3595.
15. (a) Magnus, P.; Exon, C.; Albaugh-Robertson, P. Tetrahedron 1985, 41, 5861.
16. (b) Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851.
17. Krafft, M. E. J. Am. Chem. Soc. 1988, 110, 968.
18. Krafft, M. E.; Juliano, C. A.; Scott, I. L.; Wright, C.; McEachin, M. D. J. Am. Chem. Soc. 1991, 113, 1693.
19. (e) Krafft, M. E.; Juliano, C. A. J. Org. Chem. 1992, 57, 5106.
20. (f) Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199.
21. (g) Castro, J.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron 1995, 51, 6541.
22. Price, M. E.; Schore, N. E. Tetrahedron Lett. 1989, 30, 5865.
23. Krafft, M. E. Tetrahedron Lett. 1988, 29, 999.
24. (a) MacWhorter, S. E.; Sampath, V.; Olmstead, M. M.; Schore, N. E. J. Org. Chem. 1988, 53, 203.
25. (b) MacWhorter, S. E.; Schore, N. E. J. Org. Chem. 1991, 56, 338.
26. (a) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838.
27. (b) Colvin, E. W. Silicon in Organic Synthesis; Butterworths: London, 1981.
28. (a) de Meijere, A.; Wessjohann, L. Synlett 1990, 20.
29. (b) Reference 1a, pp 68-69.
30. Conia, J. M.; Limasset, J. C. Bull. Soc. Chim. Fr. 1967, 1936.
31. Paquette, L. A.; Ternansky, R. J.; Balogh, D. W.; Kentgen, G. J. Am. Chem. Soc. 1983, 105, 5446.
32. Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235.
33. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.