A short synthesis of lennoxamine using a radical cascade

Organic Letters

Volumn 7, Issue 20, 2005, Pages 4389-4390

  Taniguchi, Tsuyoshi ^a   Iwasaki, Keiko ^a   Uchiyama, Masahiko ^a   Tamura, Osamu ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIOXANE DERIVATIVE; FREE RADICAL; HETEROCYCLIC COMPOUND; LENNOXAMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

DIOXANES; FREE RADICALS; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE;

EID: 26444530974     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051563o     Document Type: Article

References (26)

1. Natural 1 was isolated as a racemate, see: Valencia, E.; Freyer, A. J.; Shamma, M.; Fajardo, V. Tetrahedron Lett. 1984, 25, 599.
2. Quite recently (+)-1 was synthesized, see: (a) Comins, D. L.; Schilling, S.; Zhang, Y. Org. Lett. 2005, 7, 95.
3. For the recent syntheses of racemic 1, see: (b) Sahakitpichan, P.; Ruchirawat, S. Tetrahedron 2004, 60, 4169.
4. (c) Kim, G.; Kim, J. H.; Kim, W.-J.; Kim, Y. A. Tetrahedron Lett. 2003, 44, 8207.
5. (d) Koseki, Y.; Katsura, S.; Kusano, S.; Sakata, H.; Sato, H.; Monzene, Y.; Nagasaka, T. Heterocycles 2003, 59, 527.
6. (e) Fuchs, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3923.
7. (f) Ruchirawat, S.; Sahakitpichan, P. Tetrahedron Lett. 2000, 41, 8007.
8. (g) Couture, A.; Deniau, E.; Grandclaudon, P. Hoarau, C. Tetrahedron 2000, 56, 1491.
9. (h) Koseki, Y.; Kusano, S.; Sakata, H.; Nagasaka, T. Tetrahedron Lett. 1999, 40, 2169.
10. (i) Ishibashi, H.; Kawanami, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 817.
11. (a) Ishibashi, H.; Kato, I.; Takeda, Y.; Kogure, M.; Tamura, O. Chem. Commun. 2000, 1527.
12. (b) Taniguchi, T.; Ishita, A.; Uchiyama, M.; Tamura, O.; Muraoka, O.; Tanabe, G.; Ishibasi, H. J. Org. Chem. 2005, 70, 1922.
13. See also: (c) Kamimura, A.; Taguchi, Y.; Omata, Y.; Hagihara, M. J. Org. Chem. 2003, 68, 4996.
14. For reviews on radical cascades, see: (a) McCarroll, A. J.; Walton, J. C. Angew. Chem., Int. Ed. 2001, 40, 2225.
15. (b) J. Chem. Soc., Perkin Trans. 1 2001, 3215.
16. For a radical cascade involving endo-selective aryl radical cyclization onto enamide, see: (c) Ishibashi, H.; Ishita, A.; Tamura, O. Tetrahedron Lett. 2002, 43, 473. See also, ref 3b.
17. For recent references on homolytic aromatic substitution, see: (a) Ohno, H.; Iwasaki, H.; Eguchi, T.; Tanaka, T. Chem. Commun. 2004, 2228.
18. (b) Bennasar, M.-L.; Roca, T.; Ferrando, F. Tetrahedron Lett. 2004, 45, 5605.
19. (c) Beckwith, A. L. J.; Bowry, V. W.; Bowman, W. R.; Mann, E.; Parr, J.; Storey, J. M. D. Angew. Chem., Int. Ed. 2004, 43, 95 and references therein.
20. Tietze, L. F.; Schirok, H. J. Am. Chem. Soc. 1999, 121, 10264.
21. García, A.; Rodríguez, D.; Castedo, L.; Saá, C.; Domínguez, D. Tetrahedron Lett. 2001, 42, 1903.
22. For an example of radical addition of an α-amidoyl radical onto an aromatic ring, see: Gribble, G. W.; Fraser, H. L.; Badenock, J. C. Chem. Commun. 2001, 805.
23. For examples of homolytic aromatic substitution using irradiation of ditin with sunlamp, see: (a) Marion, F.; Courillion, C.; Malacria, M. Org. Lett. 2003, 5, 5095.
24. (b) Bennasar, M.-L.; Roca, T.; Griera, R.; Bosch, J. J. Org. Chem. 2001, 66, 7547.
25. (c) Bowman, W. R.; Bridge, C. F.; Cloonan, M. O.; Leach, D. C. Synlett 2001, 765.
26. (d) Josien, H.; Ko, S.-B.; Bom, D.; Curran, D. P. Chem. Eur. J. 1998, 4, 67. See also ref 5b.