Intramolecular photocycloaddition of N-alkenyl substituted maleimides: A potential tool for the rapid construction of perhydroazaazulene alkaloids

European Journal of Organic Chemistry

Volumn , Issue 8, 2001, Pages 1473-1482

  Booker Milburn, Kevin I ^a   Anson, Christopher E ^b   Clissold, Cole ^a   Costin, Nicola J ^b   Dainty, Richard F ^a   Murray, Martin ^a   Patel, Dhiren ^a   Sharpe, Andrew ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Alkaloids; Cycloadditions; Maleimides; Nitrogen heterocycles; Photochemistry

Indexed keywords

ALKALOID DERIVATIVE; AZULENE DERIVATIVE; MALEIMIDE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; ULTRAVIOLET IRRADIATION;

EID: 0035044556     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200104)2001:8<1473::aid-ejoc1473>3.0.co;2-w     Document Type: Article

References (24)

1. For a comprehensive review on the chemistry of the Stemona and related alkaloids see: R. A. Pilli, M. C. Ferreira de Oliveira, Nat. Prod. Rep. 2000, 17, 117-127.
2. L. F. Tietze, H. Schirok, M. Wohrmann, K. Schrader, Eur. J. Org. Chem. 2000, 2433-2444.
3. H. Iida, T. Takarai, C. Kibayashi, J. Org. Chem. 1978, 43, 975-979.
4. N. Langlois, Heterocycles 1990, 30, 659-664.
5. [5a] K. I. Booker-Milburn, J. K. Cowell, A. Sharpe, F. Delgado Jiménez, Chem. Commun. 1996, 249-251.
6. [5b] K. I. Booker-Milburn, S. Gulten, A. Sharpe, Chem. Commun. 1997, 1385-1386.
7. [5c] K. I. Booker-Milburn, J. K. Cowell, F. Delgado Jiménez, A. Sharpe, A. J. White, Tetrahedron 1999, 55, 5875-5888.
8. [6a] P. H. Mazzocchi, M. Bowen, N. Narain, J. Am. Chem. Soc. 1977, 99, 7063-7064.
9. [6b] P. H. Mazzocchi, S. Minamikana, P. Wilson, J. Org. Chem. 1979, 44, 1186-1188.
10. [6c] P. H. Mazzocchi, S. Minamikana, P. Wilson, M. Bowen, N. Narain, J. Org. Chem. 1981, 46, 4846-4851.
11. [6d] P. H. Mazzocchi, F. Khachik, P. Wilson, J. Am. Chem. Soc. 1981, 103, 6498-6499.
12. [6e] P. H. Mazzocchi, P. Wilson, F. Khachik, L. Klingler, S. Minamikana, J. Org. Chem. 1983, 48, 2981-2989.
13. K. Maruyama and Y. Kubo, Chem. Lett. 1978, 769-772.
14. K. I. Booker-Milburn, N. J. Costin, R. F. Dainty, D. Patel, A. Sharpe, Tetrahedron Lett. 1998, 39, 7423-7426.
15. Although MS and spectral data suggested the [2+2] dimer was formed, rigorous structural assignment was not possible due to the fact that the product was obtained as a complex mixture of stereo- and possibly regioisomers.
16. L. M. Konzelman, R. T. Conley, J. Org. Chem. 1968, 33, 3828-3838.
17. J. Hartmann, M. Schlosser, Helv. Chim. Acta 1976, 59, 453-466.
18. D. P. Curran, H. Liu, J. Chem. Soc., Perkin Trans. 1 1994, 1377-1393.
19. Y. Yamamoto, R. J. Gargiulo, D. S. Tarbell, J. Org. Chem. 1971, 36, 846-848.
20. T. Ikeda, S. Yue, R. Hutchinson, J. Org. Chem. 1985, 50, 5193-5199.
21. A. R. Battersby, S. W. Westwood, J. Chem. Soc., Perkin Trans. 1 1987, 1679-1687.
22. W. Li, C. E. Hanou, A. d'Auignon, K. D. Moeller, J. Org. Chem. 1995, 60, 8155-8170.
23. K. Matami, Tetrahedron: Asymmetry 1991, 2, 1403-1412.
24. Y. L. Chow, Y. M. A. Naguib, J. Chem. Soc., Perkin Trans. 1 1984, 1165-1171.