Dramatically different photochemical behaviour of 1-aroyl-2-methylene piperidine and pyrrolidine derivatives. An expeditious synthesis of ruspolinone

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7749-7752

  Couture, A ^a   Deniau, E ^a   Grandclaudon, P ^a   Lebrun, S ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; RUSPOLINONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY;

EID: 0030597206     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01765-0     Document Type: Article

References (37)

1. 1. (a) de la Lande, I.S. Aust. J. Exp. Biol. Med. Sci. 1948, 26, 181-187;
2. (b) Al-Shamma, D.; Drake, S.D.; Guagliardi, L.E.; Mitscher, L.A.; Swayze, J.K. Phytochemistry 1982, 21, 485-487;
3. (c) Krmpotic, E.; Farnsworth, N.R.; Messner, W.M. J. Pharm.Sci. 1972, 61, 1508-1509;
4. (d) Hoffman, J.J.; Luzbetak, D.J.; Torrance, S.J.; Cole, J.R. Phytochemistry 1978, 77, 1448.
5. 2. Kinefeli, F.; Mayer, K.K.; Poettinger, T.; Stoeber, G.; Wiegrebe, W. Arch. Pharm. 1983, 316, 773-781.
6. 3. (a) Wattney, J.; Doebel, K.J. (Geigy, J.R., A.-G) S. African 68 07 200/1969 (Chem. Abstr. 1970, 72, 3396;
7. (b) Kupchan, S.M.; Flouret, G.R.; Matuszak, C. A. J. Org. Chem. 1966, 31, 1707-1713;
8. (c) Gaur, S.P.; Jain, P.C.; Anand, N. Indian J. Chem. 1982, 21B,46-61.
9. 4. Nordlander, J.E.; Payne, M.J.; Balk, M.A.; Larkos, G.O.; Vishwanath, V.M. J. Org. Chem. 1984, 49, 4107-4117.
10. 5. Kupchan, S.M.; Balon, A.D.J.; de Grazia, C.G. J. Org. Chem. 1966, 37, 1713-1716.
11. 6. Iwao, M.; Mahalanabis, K.K.; Watanabe, M.; De Silva, S.O.; Snieckus, V. Tetrahedron 1983, 39, 1955-1962.
12. 7. Clark, R.D.; Jahangir; Langston, J.A. Can. J. Chem. 1994, 72, 23-31.
13. 8. Newcomb, M.; Esker, J.L. Tetrahedron Lett. 1991, 32, 1035-1038.
14. 9. Bradsher, C.K.; Beavers, L.E. J. Am. Chem. Soc. 1955, 77, 4812-4813.
15. 10. Ninomiya, I.; Naito, T. in The Alkaloids, Brossi, A. Ed.; Academic Press: New York, 1983; pp. 189-279.
16. 11. (a) Breederveld, M. Rec. Trav. Chim. Pays-Bas 1960, 79, 1197-1201;
17. (b) Berthon, L.; Uguen, D.; Tetrahedron Lett. 1985, 26, 3975-3978;
18. (c) Rigby, J.H.; Gupta, V. Synlett 1995, 547-548;
19. (d) Palomo, C.; Aizpura, J.M.; Legido, M.; Picard, J.P.; Dunogues, J.; Constantieux, T. Tetrahedron Lett. 1992, 33, 3903-3906;
20. (e) Cuevas, J. C.; Patil, P.; Snieckus, V. Tetrahedron Lett. 1989, 30, 5841-5844.
21. 12. (a) Yang, N.C.; Lenz, G.R. Tetrahedron Lett. 1967, 4897-4900;
22. (b) Bellus, D. Adv. Photochemistry 1978, 8, 109-113.
23. 13. (a) Gramain, J.C.; Mavel, S.; Troin, Y.; Vallée-Goyet, D. Tetrahedron 1991, 47, 7287-7300;
24. (b) Gramain, J.C.; Troin, Y.; Vallée-Goyet, D. Ibid 1991, 47, 7301-7308.
25. 14. Corey, F.J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495-498.
26. 15. (a) Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306-312;
27. (b) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
28. 16. Warren, S.; Clayden, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 241-270.
29. 17. (a) Bakker, B.H.; Tjin A-Lim, D.S.; van der Gen, A. Tetrahedron Lett. 1984, 25, 4259-4262;
30. (b) Broekhof, N.L.J.M.; Jonkers, F.L.; van der Gen, A. Tetrahedron Lett. 1979, 2433-2436;
31. (c) Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron Lett. 1993, 34, 1479-1482.
32. 18. Couture, A.; Deniau, E.; Woisel, P.; Grandclaudon, P. Tetrahedron Lett. 1995, 36, 2483-2486.
33. 19. Claxton, G.P.; Allen, L.; Grisar, J.M. Org. Synth. Coll. Vol. VI, 1988, 968-971.
34. 20. Ogawa, K.; Nomura, Y.; Takeuchi, Y.; Tomoda, S. J. Chem. Soc., Perkin Trans. 1 1982, 3031-3035.
35. 3 55.9.
36. 22. Roessler, F.; Ganzinger, D.; Johne, S.; Schöpp, E.; Hesse, M. Helv. Chim. Acta 1978, 61, 1200-1206.
37. 23. Brown, D.S.; Charreau, P.; Hansson, T.; Ley, S.V. Tetrahedron 1991, 47, 1311-1328.