Titanium(IV)-mediated tandem deprotection-cyclodehydration of protected cysteine N-amides: Biomimetic syntheses of thiazoline- and thiazole-containing heterocycles

Organic Letters

Volumn 2, Issue 21, 2000, Pages 3289-3292

  Raman, Prakash ^a   Razavi, Hossein ^a   Kelly, Jeffery W ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CYSTEINE; HETEROCYCLIC COMPOUND; THIAZOLE DERIVATIVE; TITANIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MOLECULAR MIMICRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMIDES; CRYSTALLOGRAPHY, X-RAY; CYSTEINE; HETEROCYCLIC COMPOUNDS; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; THIAZOLES; TITANIUM;

EID: 0034687195     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000178q     Document Type: Article

References (41)

1. (a) Carmeli, S.; Moore, R. E.; Patterson, G. M. L.; Corbett, T. H.; Valeriote, F. A. J. Am. Chem. Soc. 1990, 112, 8195.
2. (b) Carmeli, S.; Moore, R. E.; Patterson, G. M. L. Tetrahedron Lett. 1991, 32, 2593.
3. (c)Jansen, R.; Kunze, B.; Reichenbach, H.; Jurkiewicz, E.; Hunsmann, G.; Hofle, G. Liebigs Ann. Chem. 1992, 357.
4. (d) Kolter, R.; Moreno, F. Annu. Rev. Microbiol. 1992, 46, 141-163.
5. (e) Bayer, A.; Freund, S.; Nicholson, G.; Jung, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1336.
6. (f) Yorgey, P.; Lee, J.; Koerdel, J.; Vivas, E.; Warner, P.; Jebaratnam, D.; Kolter, R. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4519.
7. (g) Kobayashi, S.; Hidaka, S.; Kawamura, Y.; Ozaki, M.; Hayase, Y. J. Antibiot. 1998, 51, 323-327.
8. (h) Kobayashi, S.; Nakai, H.; Ikenishi, Y.; Sun, W.-Y.; Ozaki, M.; Hayase, Y.; Takeda, R. J. Antibiot. 1998, 51, 328-332.
9. (i) For an annual review see: Lewis, J. R. Nat. Prod. Rep. 2000, 17, 57-84.
10. (a) McGowan, D. A.; Jordis, U.; Minster, D. K.; Hecht, S. M. J. Am. Chem. Soc. 1977, 99, 8078-8079.
11. (b) Minster, D. K.; Jordis, U.; Evans, D. L.; Hecht, S. M. J. Org. Chem. 1978, 43, 1624-1626.
12. (c) Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1992, 57, 5566-5568.
13. (d) Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449-8450.
14. (e) Pattenden, G.; Thom, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 1629-1636.
15. (f) Parsons, R. L.; Heathcock, C. H. Tetrahedron Lett. 1994, 35, 1379-1382.
16. (g) Parsons, R. L. J.; Heathcock, C. H. Tetrahedron Lett. 1994, 35, 1383-1384.
17. (h) For a review see: Wipf, P. Chem. Rev. 1995, 95, 2115-2134.
18. (i) Parsons, R. L. J.; Heathcock, C. H. Synlett 1996, 1168-1170.
19. (j) Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556-6562.
20. (k) Wipf, P.; Venkatraman, S. Synlett 1997, 1-10.
21. (l) Kuriyama, N.; Akaji, K.; Kiso, Y. Tetrahedron 1997, 53, 8323-8334.
22. (m) White, J. D.; Kim, T.-S.; Nambu, M. J. Am. Chem. Soc. 1997, 119, 103-111.
23. (n) Ino, A.; Hasegawa, Y.; Murabayashi, A. Tetrahedron Lett. 1998, 39, 3509-3512.
24. (o) Akaji, K.; Kiso, Y. Tetrahedron 1999, 55, 10685-10694.
25. For a recent review, see: Sinha Roy, R.; Gehring, A. M.; Milne, J. C.; Belshaw, P. J.; Walsh, C. T. Nat. Prod. Rep. 1999, 16, 249-263.
26. (a) Hirotsu, Y.; Shiba, T.; T.; K. Bull. Chem. Soc. Jpn. 1967, 40, 2945.
27. (b) Hirotsu, Y.; Shiba, T.; Kaneko, T. Bull. Chem. Soc. Jpn. 1970, 43, 1870.
28. (c) Suzuki, N.; Izawa, Y. Bull. Chem. Soc. Jpn. 1976, 49, 3155-3158.
29. (d) Inami, K.; Shiba, T. Bull. Chem. Soc. Jpn. 1985, 58, 352.
30. (e) North, M.; Pattenden, G. Tetrahedron 1990, 46, 8267.
31. (f) Galeotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807.
32. (g) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267.
33. (h) Wipf, P.; Fritch, P. C. Tetrahedron Lett. 1994, 35, 5397.
34. (i) Lafargue, P.; Guenot, P.; Lellouche, J.-P. Synlett 1995, 171-172.
35. (j) Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908-909.
36. (k) Ino, A.; Murabayashi, A. Tetrahedron 1999, 55, 10271-10282.
37. Hudlicky, T.; Natchus, M. G. Org. Synth.: Theory Appl. 1993, 2, 1-25.
38. +) 222.0589, found 222.0591.
39. Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 1080.
40. Air oxidation of thiazoline rings in tantazole A, tantazole I, and mirabazole A during their isolation and purification has been reported to afford thiazoles (see: refs 1a and 1b).
41. Compound 13 was synthesized in solution by standard protocols using HOBT (1.1 equiv), HBTU (1.1 equiv), and DIEA (2.1 equiv) in DMF to mediate amide bond formation.