Mild and efficient Lewis acid-promoted detritylation in the synthesis of N-hydroxy amides: A concise synthesis of (-)-cobactin T

Journal of Organic Chemistry

Volumn 72, Issue 21, 2007, Pages 8123-8126

  Yang, Shyh Ming ^a   Lagu, Bharat ^a,b   Wilson, Lawrence J ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL ACTIVITIES; LEWIS ACID; N-HYDROXY SULFONAMIDES;

DERIVATIVES; SYNTHESIS (CHEMICAL); UREA;

AMIDES;

AMIDE; COBACTIN T; HYDROXAMIC ACID DERIVATIVE; HYDROXYLAMINE; LEWIS ACID; SULFONAMIDE; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; DETRITYLATION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

AZEPINES; HYDROXAMIC ACIDS; HYDROXYLAMINES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; TRITYL COMPOUNDS;

EID: 35348906102     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701411d     Document Type: Article

References (36)

1. Representative reviews, see: (a) Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Chem. Rev. 1999, 99, 2735.
2. (b) Matter, H.; Schudok, M. Curr. Opin. Drug Discovery Dev. 2004, 7, 513, and the references cited therein.
3. Walz, A. J.; Miller, M. J. Org. Lett. 2002, 4, 2047, and the references cited therein.
4. Green, T. W.; Wuts, P. G. M. Protecting Group in Organic Synthesis; John Wiley & Sons: New York, 1999; pp 102-104.
5. (a) Hanessian, S.; Moitessier, N.; Wilmouth, S. Tetrahedron 2000, 56, 7643.
6. (b) Hanessian, S.; Moitessier, N.; Gauchet, C.; Vian, M. J. Med. Chem. 2001, 44, 3066.
7. (c) Wittich, S.; Scherf, H.; Xie, C.; Brosch, G.; Loidl, P.; Gerhäuser, C.; Jung, M. J. Med. Chem. 2002, 45, 3296.
8. (d) Remiszewski, S. W.; Sambucetti, L. C.; Bair, K. W.; Bontempo, J.; Cesarz, D. J. Med. Chem. 2003, 46, 4609.
9. To the best of our knowledge, except TFA, other conditions for detritylation in the synthesis of hydroxamates, N-hydroxyl sulfonamide, and N-hydroxyamine derivatives have not been investigated yet.
10. (a) Kohli, V.; Blöcker, H.; Köster, H. Tetrahedron Lett. 1980, 21, 2683.
11. (b) Lampe, T. F.; Hofmann, H. M. R. Tetrahedron Lett. 1996, 37, 7695.
12. Haraldsson, G. G.; Stefansson, T.; Snorrason, H. Acta Chim. Scand. 1998, 52, 824.
13. Cabaret, D.; Wakselman, M. Can. J. Chem. 1990, 68, 2253.
14. Malanga, C. Chem. Ind. (London) 1987, 856.
15. 2 conditions, see: (a) Kaul, R.; Brouillette, Y.; Sajjadi, Z.; Hansford, K. A.; Lubell, W. D. J. Org. Chem. 2004, 69, 6131.
16. (b) Nigam, S. C.; Mann, A.; Taddei, M.; Wermuth, C.-G. Synth. Commun. 1989, 19, 3139.
17. 2, see: (c) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. 1997, 36, 1191.
18. 2 has been reported, see: (d) Evans, E. F.; Lewis, N. J.; Kapfer, I.; Macdonald, G.; Taylor, R. J. K. Synth. Commun. 1997, 27, 1819.
19. Compound 6 has been reported as a potent acyl-CoA cholesterol acyltransferase (ACAT) inhibitor, see (a) Trivedi, B. K.; Holmes, A.; Purchase, T. S.; Essenburg, A. D.; Hamelehle, K. L.; Krause, B. R.; Hes, M. S.; Stanfield, R. L. Bioorg. Med. Chem. Lett. 1995, 5, 2229.
20. N-Hydroxy sulfonamides, such as 15, are potent carbonic anhydrase (CA) inhibitors, see: (b) Scozzafava, A.; Supuran, C. T. J. Med. Chem. 2000, 43, 3677.
21. (c) Mincione, F.; Menabuoni, L.; Briganti, F.; Mincione, G.; Scozzafava, A.; Supuran, C. T. J. Enzyme Inhib. 1998, 13, 267.
22. (a) Hu, J.; Miller, M. J. J. Am. Chem. Soc. 1997, 119, 3462.
23. (b) Xu, Y.; Miller, M. J. J. Org. Chem. 1998, 63, 4314.
24. (a) Maurer, P. J.; Miller, M. J. J. Am. Chem. Soc. 1983, 105, 240.
25. (b) Maurer, P. J.; Miller, M. J. J. Org. Chem. 1981, 46, 2835.
26. (c) Hu, J.; Miller, M. J. Tetrahedron Lett. 1995, 36, 6379.
27. The N-allylation of O-benzyl hydroxamate moiety was predominated when the reactive allylating reagent, such as allyl bromide, was employed, see: Johnson, J. E.; Springfield, J. R.; Hwang, J. S.; Hayes, L. J.; Cunningham, W. C.; McClaugherty, D. L. J. Org. Chem. 1971, 36, 284.
28. (a) Miyabe, H.; Yoshida, K.; Yamauchi, M.; Takemoto, Y. J. Org. Chem. 2005, 70, 2148.
29. (b) Miyabe, H.; Yoshida, K.; Matsumura, A.; Yamauchi, M.; Takemoto, Y. Synlett 2003, 567.
30. Benzylidene[1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene] -dichloro(tricyclohexylphosphine)ruthenium (Grubbs II catalyst) was purchased from Aldrich.
31. For some recent reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
32. (b) Fürstner, A., Ed. Alkene Metathesis in Organic Synthesis. Springer: Berlin, 1998.
33. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
34. Schultz, A. G.; McCloskey, P. J. J. Org. Chem. 1985, 50, 5905.
35. (a) Rishel, M. J.; Hecht, S. M. Org. Lett. 2001, 3, 2867.
36. 2 (2.5 atm) and 5% Pd/C (ca. 10 mol% Pd loading), see: (b) Mirrington, R. N.; Schmalzl, K. J. J. Org. Chem. 1972, 37, 2877.