Novel intramolecular (4 + 1) and (4 + 2) annulations of halopolyenes by cascade radical reaction

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3579-3581

  Takasu, Kiyosei ^a   Kuroyanagi, Jun Ichi ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001032443     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0002323     Document Type: Article

References (24)

1. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990.
2. For a review, see: Leutens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
3. Representative examples, (a) Cobalt: Dzwiniel, T. L.; Etkin, N.; Striker, J. M. J. Am. Chem. Soc. 1999, 121, 10670-10641.
4. (b) Rhodium: O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443.
5. (b) Rhodium: O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443.
6. (c) Palladium: Trost, B. M.; Chan, D. M. J. Am. Chem. Soc. 1982, 104, 3733-3735.
7. (a) For a review, see: Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1010-1022.
8. (b) Ihara, M.; Makita, K.; Takasu, K. J. Org. Chem. 1999, 64, 1259-1264.
9. (c) Takasu, K.; Mizutani, M.; Noguchi, M.; Makita, K.; Ihara, M. J. Org. Chem. 2000, 65, 4112-4119 and references cited therein.
10. (a) Ihara, M.; Ohnishi, M.; Takano, M.; Makita, K.; Taniguchi, N.; Fukumoto, K. J. Am. Chem. Soc. 1992, 114, 4408-4410.
11. (b) Takasu, K.; Ueno, M.; Ihara, M. Tetrahedron Lett. 2000, 41, 2145-2148 and references cited therein.
12. For reviews of cascade radical reactions, see: (a) Curran D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 818-827.
13. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 7-1286.
14. (c) Malacria, M. Chem. Rev. 1996, 96, 289-306.
15. For recent examples of cascade radical reactions, see: (a) Journet, M.; Malacria, M. J. Org. Chem. 1994, 59, 6885-6886.
16. (b) Devin, P.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1998, 63, 6764-6765.
17. (c) Haney, B. P.; Curran, D. P. J. Org. Chem. 2000, 65, 2007-2013.
18. (a) Takasu, K.; Kuroyanagi, J.; Katsumata, A.; Ihara, M. Tetrahedron Lett. 1999, 40, 6277-6280.
19. (b) Toyota, M.; Yokota, M.; Ihara, M. Tetrahedron Lett. 1999, 40, 1551-1554.
20. (a) Ihara, M.; Katsumata, A.; Setsu, F.; Tokunaga, Y.; Fukumoto, K. J Org. Chem. 1996, 61, 677-684.
21. (b) Katsumata, A.; Takasu, K.; Ihara, M. Heterocycles 1999, 51, 733-736.
22. 3SnH (48 μmol) and AIBN (20 μmol) in benzene (4 mL) over 2 h using a syringe pump under reflux. After being stirred for 2 h, the solution was concentrated. The resulting residue was chromatographed on silica gel (4:1 v/v).
23. The electrolysis was carried out under conditions similar to those of ref 8a.
24. 4S 425.1659, found 425.1679.