Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 9.1 The Enantioselective Generation of Tetracyclic ABCE Intermediates by a Tandem Condensation, [3,3]-Sigmatropic Rearrangement, and Cyclization Sequence

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 7950-7960

  Kuehne, Martin E ^a   Xu, Feng ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001468665     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970207j     Document Type: Article

References (20)

1. Part 8: Kuehne, M. E.; Wang, T.; Seraphin, D. J. Org. Chem. 1996, 61, 7873.
2. Parsons, R. L.; Berk, J. D.; Kuehne, M. E. J. Org. Chem. 1993, 58, 7482.
3. For a review of Strychnos alkaloid syntheses see: Bosch, J.; Bonjoch, J.; Amat, M. Cordell, G. A., Ed. Alkaloids (Academic Press) 1996, 48, 75.
4. Kuehne, M. E.; Xu, F. J. Org. Chem. 1993, 58, 7490.
5. Kuehne, M. E.; Xu, F.; Brook, C. S. J. Org. Chem. 1994, 59, 7803.
6. Compound 1j was previously synthesized by two alternative methods. Spectroscopic comparisons with the product of the present method showed their identity. (a) Kuehne, M. E.; Matsko, T. H.; Bohnert, J. C.; Motyka, L.; Oliver-Smith, D. J. Org. Chem. 1981, 46, 2002. (b) Kuehne, M. E.; Kuehne, S. E. J. Org. Chem. 1993, 58, 4147.
7. Compound 1j was previously synthesized by two alternative methods. Spectroscopic comparisons with the product of the present method showed their identity. (a) Kuehne, M. E.; Matsko, T. H.; Bohnert, J. C.; Motyka, L.; Oliver-Smith, D. J. Org. Chem. 1981, 46, 2002. (b) Kuehne, M. E.; Kuehne, S. E. J. Org. Chem. 1993, 58, 4147.
8. Only an insignificant amount of the disubstituted tetracyle 1k was formed. Such compounds would be of interest for the synthesis of tubotaiwine-type alkaloids. Kuehne, M. E.; Frasier, D. A.; Spitzer, T. D. J. Org. Chem. 1991, 56, 2696.
9. This methodology was developed by J. Champoux and S. Cowen in our laboratories. It avoids the use of the potentially toxic thallium malonate. A full report of its scope will be published later.
10. Modified methodology of Krapcho et al.: Krapcho, A. P.; Weimaster, J. F.; Eldridge, J. M.; Jahngen, E. G. E. Jr.; Lovey, A. J.; Stephens, W. P. J. Org. Chem. 1978, 43, 138.
11. Henin, J.; Massiot, G.; Vercauteren, J. Tetrahedron Lett. 1987, 28, 1271.
12. An inventive photochemical cyclization, also starting from L-tryptophan as precursor, provided another noteworthy approach to such tetracyclic ABCE alkaloid intermediates. Winkler, J. D.; Scott, R. D.; Williard, P. G. J. Am. Chem. Soc. 1990, 112, 8971.
13. Legseir, B.; Henin, J.; Massiot, G.; Vercauteren, J. Tetrahedron Lett. 1987, 28, 3573.
14. Kuehne, M. E.; Matson, P. A.; Bornmann, W. G. J. Org. Chem. 1991, 56, 514.
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16. Kuehne, M. E.; Bandarage, U. K.; Hammach, A.; Li, Y.-L.; Wang, T. J. Org. Chem. Submitted.
17. Arai, I; Muramatsu, I. J. Org. Chem. 1983, 48, 121.
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19. Waldman, H.; Schmidt, G.; Jansen, M.; Geb, J. Tetrahedron Lett. 1993, 34, 5867 (ref 6); Tetrahedron 1994, 50, 11865.
20. Waldman, H.; Schmidt, G.; Jansen, M.; Geb, J. Tetrahedron Lett. 1993, 34, 5867 (ref 6); Tetrahedron 1994, 50, 11865.