Formal intramolecular [5 + 2] photocycloaddition reactions of maleimides: A novel approach to the CDE ring skeleton of (-)-cephalotaxine

Organic Letters

Volumn 3, Issue 19, 2001, Pages 3005-3008

  Booker Milburn, Kevin I ^a   Dudin, Leo F ^a   Anson, Christopher E ^b   Guile, Simon D ^c  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CEPHALOTAXINE; HARRINGTONINE DERIVATIVE; MALEIMIDE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; MEDICINAL PLANT; PHOTOCHEMISTRY; PLANT LEAF; SYNTHESIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; HARRINGTONINES; MALEIMIDES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHOTOCHEMISTRY; PLANT LEAVES; PLANTS, MEDICINAL;

EID: 0035922371     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016411h     Document Type: Article

References (26)

1. Paudler, W. M.; Kerley, G. I.; McKay, J. J. Org. Chem. 1963, 28, 2194-2197.
2. Arora, S. K.; Bates, R. B.; Grady, R. A.; Germain, G.; Declercq, J. P.; Powell, R. G. J. Org. Chem. 1976, 41, 551-554 and references therein.
3. For a recent total synthesis of (-)-cephalotaxine and reference to previous synthetic work in this area, see: Tietze, L. F.; Schirok, H. J. Am. Chem. Soc. 1999, 121, 10264-10269.
4. Keller, L.; Dumas, F.; d'Angelo, J. Tetrahedron. Lett. 2001, 42, 1911-1913 and references therein.
5. O'Brien, S.; Kantarjian, H.; Koller, C.; Feldman, E.; Beran, M.; Andreeff, M.; Giralt, S.; Cheson, B.; Keating, M.; Freireich, E.; Rios, M. B.; Talpaz, M. Blood 1999, 93, 4149-4153.
6. (a) Booker-Milburn, K. I.; Costin, N. J.; Dainty, R. F.; Patel, D.; Sharpe, A. Tetrahedron. Lett. 1998, 39, 7423.
7. (b) Booker-Milburn, K. I.; Anson, C. E.; Clissold, C.; Costin, N. J.; Dainty, R. F.; Murray, M.; Patel, D.; Sharpe, A. Eur. J. Org. Chem. 2001, 1473-1482.
8. Chan, T. H.; Brownbridge, P. J. Am. Chem. Soc. 1980, 102, 3534.
9. In reality a protected maleimide will be used to avoid potential problems with photodimerization (ref 6).
10. Molander, G. A.; Hiersemann, M. Tetrahedron Lett. 1997, 38, 4347.
11. Data deposited at Cambridge Crystallographic Data Centre (CCDC 158520).
12. (a) Ito, S. I.; Kasai, M.; Ziffer, H. Silverton, J. V. Can. J. Chem. 1987, 65, 574-582. (b) Piers, E.; Grierson, J. R.; Lau, C. K.; Nagakura, I. Can. J. Chem. 1982, 60, 210-223.
13. (a) Ito, S. I.; Kasai, M.; Ziffer, H. Silverton, J. V. Can. J. Chem. 1987, 65, 574-582. (b) Piers, E.; Grierson, J. R.; Lau, C. K.; Nagakura, I. Can. J. Chem. 1982, 60, 210-223.
14. (a) Eis, M. J.; Wrobel, J. E.; Ganem, B.; Bach, T.; Bergmann, H. J. Am. Chem. Soc. 1984, 106, 3693-3694. (b) Yamaguchi, M.; Shibato, K.; Hirao, I. Tetrahedron Lett. 1984, 25, 1159-1162. Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248-2256.
15. (a) Eis, M. J.; Wrobel, J. E.; Ganem, B.; Bach, T.; Bergmann, H. J. Am. Chem. Soc. 1984, 106, 3693-3694. (b) Yamaguchi, M.; Shibato, K.; Hirao, I. Tetrahedron Lett. 1984, 25, 1159-1162. Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248-2256.
16. (a) Eis, M. J.; Wrobel, J. E.; Ganem, B.; Bach, T.; Bergmann, H. J. Am. Chem. Soc. 1984, 106, 3693-3694. (b) Yamaguchi, M.; Shibato, K.; Hirao, I. Tetrahedron Lett. 1984, 25, 1159-1162. Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248-2256.
17. Allsop, A.; Brooks, G., Edwards, P. D.; Kaura, A. C.; Southgate, R. J. Antibiot. 1996, 49, 921-928.
18. (a) Mazzocchi, P. H.; Bowen, M.; Narain, N. J. Am. Chem. Soc. 1977, 99, 7063. (b) Mazzocchi, P. H.; Minamikana, S.; Wilson, P. J. Org. Chem. 1979, 44, 1186. Mazzocchi, P. H.; Minamikana, S.; Wilson, P.; Bowen, M.; Narain, N. J. Org. Chem. 1981, 46, 4846. Mazzocchi, P. H.; Khachik, F.; Wilson, P. J. Am. Chem. Soc. 1981, 103, 6498. (e) Mazzocchi, P. H.; Wilson, P.; Khachik, F.; Klingler, L.; Minamikana, S. J. Org. Chem. 1983, 48, 2981.
19. (a) Mazzocchi, P. H.; Bowen, M.; Narain, N. J. Am. Chem. Soc. 1977, 99, 7063. (b) Mazzocchi, P. H.; Minamikana, S.; Wilson, P. J. Org. Chem. 1979, 44, 1186. Mazzocchi, P. H.; Minamikana, S.; Wilson, P.; Bowen, M.; Narain, N. J. Org. Chem. 1981, 46, 4846. Mazzocchi, P. H.; Khachik, F.; Wilson, P. J. Am. Chem. Soc. 1981, 103, 6498. (e) Mazzocchi, P. H.; Wilson, P.; Khachik, F.; Klingler, L.; Minamikana, S. J. Org. Chem. 1983, 48, 2981.
20. (a) Mazzocchi, P. H.; Bowen, M.; Narain, N. J. Am. Chem. Soc. 1977, 99, 7063. (b) Mazzocchi, P. H.; Minamikana, S.; Wilson, P. J. Org. Chem. 1979, 44, 1186. Mazzocchi, P. H.; Minamikana, S.; Wilson, P.; Bowen, M.; Narain, N. J. Org. Chem. 1981, 46, 4846. Mazzocchi, P. H.; Khachik, F.; Wilson, P. J. Am. Chem. Soc. 1981, 103, 6498. (e) Mazzocchi, P. H.; Wilson, P.; Khachik, F.; Klingler, L.; Minamikana, S. J. Org. Chem. 1983, 48, 2981.
21. (a) Mazzocchi, P. H.; Bowen, M.; Narain, N. J. Am. Chem. Soc. 1977, 99, 7063. (b) Mazzocchi, P. H.; Minamikana, S.; Wilson, P. J. Org. Chem. 1979, 44, 1186. Mazzocchi, P. H.; Minamikana, S.; Wilson, P.; Bowen, M.; Narain, N. J. Org. Chem. 1981, 46, 4846. Mazzocchi, P. H.; Khachik, F.; Wilson, P. J. Am. Chem. Soc. 1981, 103, 6498. (e) Mazzocchi, P. H.; Wilson, P.; Khachik, F.; Klingler, L.; Minamikana, S. J. Org. Chem. 1983, 48, 2981.
22. (a) Mazzocchi, P. H.; Bowen, M.; Narain, N. J. Am. Chem. Soc. 1977, 99, 7063. (b) Mazzocchi, P. H.; Minamikana, S.; Wilson, P. J. Org. Chem. 1979, 44, 1186. Mazzocchi, P. H.; Minamikana, S.; Wilson, P.; Bowen, M.; Narain, N. J. Org. Chem. 1981, 46, 4846. Mazzocchi, P. H.; Khachik, F.; Wilson, P. J. Am. Chem. Soc. 1981, 103, 6498. (e) Mazzocchi, P. H.; Wilson, P.; Khachik, F.; Klingler, L.; Minamikana, S. J. Org. Chem. 1983, 48, 2981.
23. Pyrex-filtered UV light from a 125-W medium-pressure Hg lamp was used throughout this study (see ret 6 for full details). The maleimides used in this and previous studies all have characteristic UV absorptions at 210-240 nm (strong) and 290-310 nm (weak). As a Pyrex-filtered UV source is used (>290 nm) it is likely that photocycloaddition arises from absorption in the 290-310 nm region.
24. For previous examples of photocycloadditions controlled by H-bonding, see: (a) Bach, T.; Bergmann, H. J. Am. Chem. Soc. 2000, 122, 11525. (b) Bach, T.; Bergmann, H.; Harms, K. J. Am. Chem. Soc. 1999, 121, 10650.
25. For previous examples of photocycloadditions controlled by H-bonding, see: (a) Bach, T.; Bergmann, H. J. Am. Chem. Soc. 2000, 122, 11525. (b) Bach, T.; Bergmann, H.; Harms, K. J. Am. Chem. Soc. 1999, 121, 10650.
26. For previous examples of photocycloadditions controlled by H-bonding, see: (a) Bach, T.; Bergmann, H. J. Am. Chem. Soc. 2000, 122, 11525. (b) Bach, T.; Bergmann, H.; Harms, K. J. Am. Chem. Soc. 1999, 121, 10650.