Amino acid-based dithiazines: Synthesis and photofragmentation of their benzaldehyde adducts

Organic Letters

Volumn 4, Issue 23, 2002, Pages 4129-4131

  Kurchan, Alexei N ^a   Kutateladze, Andrei G ^a  

^a UNIVERSITY OF DENVER   (United States)

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ARTICLE;

EID: 0042236983     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0268790     Document Type: Article

References (21)

1. (a) McHale, W. A.; Kutateladze, A. G. J. Org. Chem. 1998, 63, 9924.
2. (b) Vath, P.; Falvey, D. E.; Barnhurst, L. A.; Kutateladze, A. G. J. Org. Chem. 2001, 66, 2886.
3. (a) Wan, Y.; Mitkin, O.; Barnhurst, L.; Kurchan, A.; Kutateladze, A. Org. Lett. 2000, 2, 3817.
4. (b) Mitkin, O. D.; Kurchan, A. N.; Wan, Y.; Schiwal, B. F.; Kutateladze, A. G. Org. Lett. 2001, 3, 1841.
5. (c) Mitkin, O.; Wan, Y.; Kurchan, A.; Kutateladze, A. Synthesis 2001, 1133.
6. (d) Barnhurst, L. A.; Kutateladze, A. G. Org. Lett. 2001, 3, 2633.
7. (e) Wan, Y.; Angleson, J. K.; Kutateladze, A. G. J. Am. Chem. Soc. 2002, 124, 5610.
8. First synthesized: Braithwaite, E. R.; Graymore, J. J. Chem. Soc. 1953, 143.
9. (a) Bauermeister, H.; Riechers, H.; Schomberg, D.; Washausen, P.; Winterfeldt, E. Angew. Chem., Int. Ed. Engl. 1991, 30, 191.
10. (b) Redlich, H.; Lenfers, J. B. Liebigs Ann. Chem. 1988, 597.
11. (c) Flores-Parra, A.; Khuong-Huu, F. Tetrahedron 1986, 42, 5925.
12. (d) Paulsen, H.; Mielke, B.; Von Deyn, W. Liebigs Ann. Chem. 1987, 439
13. (e) Brown, C. A.; Chapa, O.; Yamaichi, A. Heterocycles 1982, 18, 187.
14. (a) Kumar, A.; Coe, P. L.; Jones, A. S.; Walker, R. T.; Balzarini, J.; De Clercq, Eric. J. Med. Chem. 1990, 33, 2368.
15. (b) Juaristi, E.; Gonzalez, E. A.; Pinto, B. M.; Johnston, B. D.; Nagelkerke, R. J. Am. Chem. Soc. 1989, 111, 6745.
16. Balanson, R. D.; Kobal, V. M.; Schumaker, R. R. J. Org. Chem. 1977, 42, 393.
17. Cadenas-Pliego, G.; de Jesus Rosales-Hoz, M.; Contreras, R.; Flores-Parra, A. Tetrahedron: Asymmetry 1994, 5, 633.
18. Werkhoff, P.; Guentert, M.; Hopp, R. Food Rev. Int. 1992, 8, 391.
19. 4, and the solvent was removed under reduced pressure. Resulting products were purified by recrystallization or flash chromatography (for further details and spectra, see Supporting Information; this procedure is a modification of the N-merthyldithiazine synthesis described in ref 5b).
20. Seebach, D.; Corey, E. J. J. Org. Chem. 1975, 40, 231.
21. 4. The solvent was removed under reduced pressure, and the product was purified by flash chromatography using chloroform as an eluent. (For further details and spectra, see Supporting Information.)