Selective substitutions in the C10-methyl group in erythromycin derivatives

Tetrahedron

Volumn 62, Issue 25, 2006, Pages 6090-6099

  Gunnes, Sølvi ^a   Rømming, Christian ^a   Undheim, Kjell ^a  

^a UNIVERSITY OF OSLO   (Norway)

Author keywords

Allylic bromination; C10 methyl amination; C10 methyl homologation; Chemoselective N oxidation; Pd catalysed cross couplings

Indexed keywords

10 (2 ETHOXYPROP 2 EN 1 YL)METHYL 10 DESMETHYLERYTHRALOSAMINE; 10 (2 FURYL)METHYL 10 DESMETHYLERYTHRALOSAMINE; 10 (2 OXOPROPYL) 10 DESMETHYLERYTHRALOSAMINE; 10 (3 PHENYLPROP 1 YLAMINOMETHYL) 10 DESMETHYLERYTHRALOSAMINE; 10 BENZYL 10 DESMETHYLERYTHRALOSAMINE; 10 BENZYLAMINOMETHYL 10 DESMETHYLERYTHRALOSAMINE; 10 BROMOMETHYL 10 DESMETHYLERYTHRALOSAMINE; 10 BROMOMETHYL 10 DESMETHYLERYTHRALOSAMINE N OXIDE; 10 BROMOMETHYL 2'O 3O BIS(TERT BUTYLDIMETHYLSILYL) 10 DESMETHYLERYTHRALOSAMINE; 10 ETHYL 2'O 3O BIS(TERT BUTYLDIMETHYLSILYL) 10 DESMETHYLERYTHRALOSAMINE; 10,11 EPOXYERYTHRALOSAMINE N OXIDE; 10,11 ERYTHRALOSAMINE; 2'O ACETYL 8 BROMOERYTHRALOSAMINE; ACETIC ACID; ERYTHRALOSAMINE; ERYTHRALOSAMINE N OXIDE; ERYTHROMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 33646571847     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.03.098     Document Type: Article

References (16)

1. Asaka T., Manaka A., and Sugiyama H. Curr. Top. Med. Chem. 3 (2003) 961-989
2. Wu Y.-J., and Su W.-G. Curr. Med. Chem. 8 (2001) 1727-1758
3. Katz L., and Ashley G.W. Chem. Rev. 105 (2005) 499-527
4. Ruan X., Pereda A., Stassi D.L., Zeidner D., Summers R.G., Jackson M., Shivakumar A., Kakavas S., Staver M.J., Donadio S., and Katz L. J. Bacteriol. 179 (1997) 6416-6425
5. Katz, L.; Stassi, D. L.; Summers, R. G.; Ruan, X.; Pereda-Lopez, A.; Kakavas, S. PCT 1998, WO 98/51695.
6. Gu Y.G., Zhang X., Clark R.F., Djuric S.W., and Ma Z. Tetrahedron Lett. 45 (2004) 3051-3053
7. Flynn E.H., Sigal M.V., Wiley P.F., and Gerzon K. J. Am. Chem. Soc. 76 (1954) 3121-3131
8. Kurath P., Jones P.H., Egan R.S., and Perum T. Experientia 27 (1971) 362
9. Omura S., Tsuzuki K., Sunazuka T., Marui S., Toyoda H., Inatomi N., and Itoh Z. J. Med. Chem. 30 (1987) 1941-1943
10. Auricchio S., Fronza G., Meille S.V., Mele A., and Favara D. J. Org. Chem. 56 (1991) 2250-2253
11. Baker W.R., Clark J.D., Stephens R.L., and Kim K.H. J. Org. Chem. 53 (1988) 2340-2345
12. Stenmark H.G., Brazzale A., and Ma Z.K. J. Org. Chem. 65 (2000) 3875-3876
13. Freiberg, L. A. Ger. Offen. 2,154,032, 15 pp, 1972 [Chem. Abstr. 1972, 19965e].
14. SMART and SAINT. Area-Detector Control and Integration Software Version 5.054 (1998), Bruker Analytical X-ray Instruments, Madison, WI
15. Sheldrick G.M. SADABS Version 2.01. Program for Empirical Correction of Area Detector Data (2000), University of Göttingen, Germany
16. Sheldrick G.M. SHELXTL, Structure Determination Programs Version 5.10 (1997), Bruker Analytical X-ray Instruments, Madison, WI