Formation of hydrindans and tricyclo[4.3.0.03,8]nonanes via 6-endo trapping of the Nazarov oxyallyl intermediate

Synlett

Volumn , Issue 9, 1999, Pages 1363-1366

  Browder, C C ^a   West, F G ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Cyclizations; Domino reactions; Polycycles; Ring closure; Tandem reactions

Indexed keywords

ALKENE DERIVATIVE; BORON DERIVATIVE; CATION; HYDRINDAN DERIVATIVE; INDAN DERIVATIVE; KETONE DERIVATIVE; TITANIUM DERIVATIVE; TRICYCLO[4.3.0.0]NONANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032874841     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-32132     Document Type: Article

References (26)

1. th National Meeting of the American Chemical Society, San Francisco, CA, April 1997; American Chemical Society: Washington, DC, 1997; ORGN 511.
2. (a) Bunce, R. A. Tetrahedron 1995, 51, 13103.
3. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
4. (c) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992.
5. Reviews: (a) Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. (N.Y.) 1994, 45, 1.
6. (b) Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp. 751-784.
7. (c) Ramaiah, M. Synthesis 1984, 529.
8. (d) Santelli-Rouvier, C.; Santelli, M. Synthesis 1983, 429.
9. (e) See also: Tius, M. A. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1994; Vol. 14, pp. 583-630.
10. Blize, A. E.; Bender, J. A.; Browder, C. C.; Giese, S.; West, F. G. J. Org. Chem. 1998, 63, 2430.
11. (a) Giese, S.; West, F. G. Tetrahedron Lett. 1998, 39, 8393.
12. (b) Wang, Y.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, 876.
13. West, F. G.; Fisher, P. V.; Arif, A. M. J. Am. Chem. Soc. 1993, 115, 1595.
14. Trienones 1a-g were synthesized in five steps from 4-methylpent-4-enal by a route analogous to that previously described in ref. 4. For synthesis of 4-methylpent-4-enal, see: Baker, R.; Brimble, M. A. J. Chem. Soc. Perkin Trans. 1 1988, 125.
15. 22O: C, 82.52; H, 10.16. Found C, 82.64; H, 10.14.
16. The spectral data for the known endocyclic isomer of 2a were identical with those previously reported: Fringuelli, F.; Pizzo, F.; Taticchi, A.; Halls, T. D. J.; Wenkert, E. J. Org. Chem. 1982, 47, 5056.
17. Bender, J. A.; Arif, A. M.; West, F. G. J. Am. Chem. Soc. 1999, 121, in press.
18. 12 have observed intramolecular 3+2 trapping of oxyallyl cations by pendant dienes in some cases.
19. Harmata, M.; Carter, K. W. Tetrahedron Lett. 1997, 38, 7985.
20. (a) Review: Kellogg, R. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp. 79-103.
21. (b) For a related case involving apparent hydride transfer during a Nazarov cyclization, see: Denmark, S. E.; Habermas, K. L.; Hite, G. A. Helv. Chim. Acta 1988, 71, 168.
22. 4-generated carbocations, see: (a) Engler, T. A.; Ali, M. H.; Takusagawa, F. J. Org. Chem. 1996, 61, 8456.
23. (b) Harmata, M.; Elomari, S.; Barnes, C. L. J. Am. Chem. Soc. 1996, 118, 2860.
24. (c) Harmata, M.; Gamlath, C, B.; Barnes, C. L.; Jones, D. E. J. Org. Chem. 1995, 60, 5077.
25. (d) Willmore, N. D.; Goodman, R.; Lee, H-H.; Kennedy, R. M. J. Org. Chem. 1992, 57, 1216.
26. + incorporation in the silicon-directed Nazarov cyclization, see: Denmark, S. E.; Klix, R. C.; Tetrahedron 1988, 44, 4043.