Synthesis of N-[2-(2-pyridyl)ethyl]-17a-aza-D-homosteroids and their biomimetic copper-mediated ligand hydroxylations with molecular oxygen

Tetrahedron Asymmetry

Volumn 14, Issue 13, 2003, Pages 1925-1934

  Magyar, Angéla ^a   Schönecker, Bruno ^b   Wölfling, János ^a   Schneider, Gyula ^a   Günther, Wolfgang ^b   Görls, Helmar ^b  

^a UNIVERSITY OF SZEGED   (Hungary)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

16ALPHA HYDROXY 3 METHOXY N [2 (2 PYRIDYL)ETHYL] 17A AZA DEXTRO HOMOESTRA 1,3,5(10) TRIENE; 3 METHOXY N [2 (2 PYRIDYL)HYDROXYLETHYL] 17A AZA DEXTRO HOMOESTRA 1,3,5(10) TRIENE; COPPER COMPLEX; ESTRONE DERIVATIVE; HOMOSTEROID; OXIME; OXYGEN; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BECKMANN REARRANGEMENT; BINDING AFFINITY; BIOMIMETICS; CHIRALITY; EPIMER; HYDROXYLATION; MOLECULAR BIOLOGY; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038482053     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00362-8     Document Type: Article

References (30)

1. Kitajima N., Moro-oka Y. Chem. Rev. 94:1994;737-757.
2. Klinman J.P. Chem. Rev. 96:1996;2541-2561 Kaim, W.; Rall, J. Angew. Chem. 1996, 108, 47-64; Angew. Chem., Int. Ed. Engl. 1996, 35, 43-60.
3. Karlin K.D., Kaderli S., Zuberbühler A.D. Acc. Chem. Res. 30:1997;139-147.
4. Than R., Feldmann A., Krebs B. Coord. Chem. Rev. 182:1999;211-241.
5. Holland P.L., Tolman W.P. Coord. Chem. Rev. 190-192:1999;855-869.
6. Schindler S. Eur. J. Inorg. Chem. 2000;2311-2326 Que, L., Jr.; Tolmann, W. B. Angew. Chem. 2002, 114, 1160-1185; Angew. Chem., Int. Ed. 2002, 41, 1114-1137.
7. Amadéi E., Alilou E.H., Eydoux F., Pierrot M., Réglier M., Waegell B. J. Chem. Soc., Chem. Commun. 1992;1782-1784.
8. Itoh S., Kondo T., Komatsu M., Ohshiro Y., Li C., Kanehisa N., Kai Y., Fukuzumi S. J. Am. Chem. Soc. 117:1995;4714-4715.
9. Blain I., Bruno P., Giorgi M., Lojou E., Lexa D., Réglier M. Eur. J. Inorg. Chem. 1998;1297-1304.
10. Itoh S., Nakao H., Berreau L.M., Kondo T., Komatsu M., Fukuzumi S. J. Am. Chem. Soc. 120:1998;2890-2899.
11. Obias H.V., Lin Y., Murthy N.N., Pidcock E., Solomon E.I., Ralle M., Blackburn N.J., Neuhold Y.-M., Zuberbühler A.D., Karlin K.D. J. Am. Chem. Soc. 120:1998;12960-12961.
12. Blain I., Giorgi M., DeRiggi I., Réglier M. Eur. J. Inorg. Chem. 2001;205-211.
13. Itoh, S.; Taki, M.; Nakao, H.; Holland, P. L. Tolman, W. B.; Que, L., Jr.; Fukuzumi, S. Angew. Chem. 2000, 112, 409-411; Angew. Chem., Int. Ed. 2000, 39, 398-400;
14. Blain I., Giorgi M., DeRiggi I., Réglier M. Eur. J. Inorg. Chem. 2000;393-398.
15. Gonschior M., Kötteritzsch M., Rost M., Schönecker B., Wyrwa R. Tetrahedron: Asymmetry. 11:2000;2159-2182 Schönecker, B.; Zheldakova, T.; Liu, Y.; Köttevitzseh, M.; Gunther, W.; Görls, H. Angew. Chem., in press.
16. Schönecker B., Lange C., Kötteritzsch M., Günther W., Weston J., Anders E., Görls H. J. Org. Chem. 65:2000;5487-5497.
17. Anliker R., Müller M., Wohlfahrt J., Heusser H. Helvet. Chim. Acta. 38:1955;1404-1409.
18. Kaufmann St. J. Am. Chem. Soc. 73:1951;1779-1780.
19. Regan B.M., Hayes F.N. J. Am. Chem. Soc. 78:1956;639-643.
20. Robinson C.H., Gnoj O., Mitchell A., Oliveto E.P. Tetrahedron. 21:1965;743-757.
21. Carman R.M., Cowley D. Austr. J. Chem. 18:1965;213-217.
22. Klinot J., Vystrčil A. Coll. Czech. Chem. Commun. 27:1962;377-386.
23. Fenselau A.H., Hamamura E.H., Moffat J.G. J. Org. Chem. 35:1970;3546-3552.
24. Cervantes A., Crabbé P., Iriarte J., Rosenkranz G. J. Org. Chem. 33:1968;4294-4296.
25. Borch L.F. Tetrahedron Lett. 9:1968;61-65.
26. COLLECT, Data Collection Software; Nonius BV, Netherlands, 1998.
27. Otwinowski; Z.; Minor, W. In Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A; Carter, C. W.; Sweet, R. M., eds. Processing of X-Ray Diffraction Data Collected in Oscillation Mode; Academic Press: New York, 1997; pp. 307-326.
28. Sheldrick G.M. Acta Crystallogr., Sect. A. 46:1990;467-473.
29. Sheldrick, G. M. SHELXL-97 (Release 97-2), University of Göttingen, Germany, 1997.
30. CCDC 205992 and 205993 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk).