LC-(TIC/EIC)-MS as tool in the analysis of diastereomeric 3,12-aza-analogues of deoxycholic acid

Arkivoc

Volumn 2007, Issue 10, 2007, Pages 325-336

  Verzele, Dieter ^a   Goeman, Jan L ^a   Madder, Annemieke ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Alloc deprotection; Dipodal scaffold; LC MS; Steroids; TIC EIC detection

Indexed keywords

EID: 34247564652     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.a21     Document Type: Article

References (31)

1. Verzele, D.; Madder, A. Eur. J. Org. Chem. 2007, doi: 10.1002/ejoc.200600972.
2. (a) Cheng, Y. A.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813.
3. (b) Barry, J. F.; Davis, A. P.; Pérez-Payán, M. N.; Elsegood, M. R. J.; Jackson, R. F. W.; Gennari, C.; Piarulli, U.; Gude, M. Tetrahedron Lett. 1999, 40, 2849.
4. (c) Zhou, X.; Rehman, A.; Li, C.; Savage, P. B. Org. Lett. 2000, 2, 3015.
5. (d) del Amo, V.; Siracusa, L.; Markidis, T.; Baragaña, B.; Bhattarai, K. M.; Galobardes, M.; Naredo, G.; Pérez-Payán, M. N.; Davis, A. P. Org. Biomol. Chem. 2004, 2, 3320.
6. For various applications and use of steroid scaffolds, see also: (e) Salunke, D. B.; Hazra, B. G.; Pore, V. S. ARKIVOC 2003, (ix), 115.
7. (f) Maltais, R.; Tremblay, M. R.; Ciobanu, L. C.; Poirier, D. J. Comb. Chem. 2004, 6, 443.
8. (g) Davis, A. P. Coord. Chem. Rev. 2006, 250, 2939.
9. (h) Bortolini, O.; Fantin, G.; Fogagnolo, M.; Maietti, S. ARKIVOC 2006, (vi), 40.
10. (i) Salunke, D. B.; Hazra, B. G.; Pore, V. S. Curr. Med. Chem. 2006, 13, 813.
11. (a) Gao, H. W.; Dias, J. R. Org. Prep. Proc. Int. 1999, 31, 145.
12. (b) Virtanen, E.; Kolehmainen, E. Eur. J. Org. Chem. 2004, 16, 3385.
13. Hsieh, H.; Muller, J. G.; Burrows, C. J. Bioorg. Med. Chem. 1995, 3, 823.
14. (a) Broderick, S.; Davis, A. P.; Williams, R. P. Tetrahedron Lett. 1998, 39, 6083.
15. (b) Li, C.; Rehman, A.; Dalley, N. K.; Savage, P. B. Tetrahedron Lett. 1999, 40, 1861.
16. (c) Davis, A. P.; Pérez-Payán, M. N. Synlett 1999, 991.
17. (d) del Amo, V.; Bhattarai, K.; Nissinen, M.; Rissanen, K.; Pérez-Payán, M. N.; Davis, A. P. Synlett 2005, 8, 1319.
18. (a) Kocieñski, P. J. Protecting Groups; Thieme: Stuttgart; New York, 1994; pp. 199-201.
19. (b) For reviews regarding allyl based protecting groups, see: Guibé, F. Tetrahedron 1997, 53, 13509
20. and 1998, 54, 2967.
21. (a) Holmes, C. P.; Jones, D. G. J. Org. Chem. 1995, 60, 2318.
22. (b) Holmes, C. P. J. Org. Chem. 1997, 62, 2370.
23. (a) Vanhoenacker, G.; Li, L.; Lynen, F.; Madder, A.; De Clercq, P.; Sandra, P. J. Sep. Sci. 2002, 25, 671.
24. (b) Madder, A.; Li, L.; De Muynck, H.; Farcy, N.; Van Haver, D.; Fant, F.; Vanhoenacker, G.; Sandra, P.; Davis, A. P.; De Clercq, P. J. J. Comb. Chem. 2002, 4, 552.
25. (a) Fernández-Forner, D.; Casals, G.; Navarro, E.; Ryder, H.; Albericio, F. Tetrahedron Lett. 2001, 42, 4471.
26. (b) Opatz, T.; Liskamp, M. J. Org. Lett. 2001, 3, 3499.
27. (a) Honda, M.; Morita, H.; Nagakura, I. J. Org. Chem. 1997, 62, 8932.
28. (b) Chamorro, C.; Hofman, J.; Liskamp, R. M. J. Tetrahedron 2004, 60, 8691.
29. Dias, J. R.; Gao, H.; Kolehmainen, E. Spectrochim. Acta A 2000, 56, 53.
30. (a) Beugelmans, R.; Bourdet, S.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 4349.
31. (b) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1995, 36, 3129.