Synthesis of 16,17-seco-steroids with iminomethyl-2-pyridine and aminomethylene-2-pyridine structures as chiral ligands for copper ions and molecular oxygen activation

Tetrahedron Asymmetry

Volumn 14, Issue 18, 2003, Pages 2705-2715

  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

ALDEHYDE DERIVATIVE; AMINE; AMINOMETHYLENE 2 PYRIDINE; CARBOXYL GROUP; CARBOXYLIC ACID; COPPER ION; IMINOMETHYL 2 PYRIDINE; LIGAND; NITRILE; OXYGEN; PYRIDINE DERIVATIVE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CURTIUS REARRANGEMENT; DEGRADATION; HYDROXYLATION; ION TRANSPORT; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 1842431678     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00539-1     Document Type: Article

References (42)

1. Kitajima N., Morooka Y. Chem. Rev. 94:1994;737-757.
2. Karlin K.D., Kaderli S., Zuberbühler A.D. Acc. Chem. Res. 30:1997;139-147.
3. Holland, P. L.; Rodgers, K. R.; Tolman, W. B. Angew. Chem. 1999, 111, 1210-1213; Angew. Chem., Int. Ed. 1999, 38, 1139-1142.
4. Holland, P. L.; Rodgers, K. R.; Tolman, W. B. Angew. Chem. 1999, 111, 1210-1213; Angew. Chem., Int. Ed. 1999, 38, 1139-1142.
5. Schindler S. Eur. J. Inorg. Chem. 2000;2311-2326.
6. Kaim, W.; Rall, J. Angew. Chem. 1996, 108, 47-64; Angew. Chem., Int. Ed. 1996, 35, 43-60.
7. Kaim, W.; Rall, J. Angew. Chem. 1996, 108, 47-64; Angew. Chem., Int. Ed. 1996, 35, 43-60.
8. Que, L., Jr.; Tolmann, W. B. Angew. Chem. 2002, 114, 1160-1185; Angew. Chem., Int. Ed. 2002, 41, 1114-1137.
9. Que, L., Jr.; Tolmann, W. B. Angew. Chem. 2002, 114, 1160-1185; Angew. Chem., Int. Ed. 2002, 41, 1114-1137.
10. Itoh S., Kondo T., Komatsu M., Ohshiro Y., Li C., Kanehisa N., Kai Y., Fukuzumi S. J. Am. Chem. Soc. 117:1995;4714-4715.
11. Blain I., Bruno P., Giorgi M., Lojou E., Lexa D., Reglier M. Eur. J. Inorg. Chem. 1998;1297-1304.
12. Itoh S., Nakao H., Berreau L.M., Kondo T., Komatsu M., Fukuzumi S. J. Am. Chem. Soc. 120:1998;2890-2899.
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. 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.
15. Blain I., Giorgi M., DeRiggi I., Reglier M. Eur. J. Inorg. Chem. 2001;205-211.
16. Blain I., Giorgi M., DeRiggi I., Réglier M. Eur. J. Inorg. Chem. 2000;393-398.
17. Gonschior M., Kötteritzsch M., Rost M., Schönecker B., Wyrwa R. Tetrahedron: Asymmetry. 11:2000;2159-2182.
18. Schönecker, B.; Zheldakova, T.; Liu, Y.; Kötteritzsch, M.; Günther, W.; Görls, H. Angew. Chem. 2003, 115, 3361-3365; Angew. Chem., Int Ed. 2003, 42, 3240-3244.
19. Schönecker, B.; Zheldakova, T.; Liu, Y.; Kötteritzsch, M.; Günther, W.; Görls, H. Angew. Chem. 2003, 115, 3361-3365; Angew. Chem., Int Ed. 2003, 42, 3240-3244.
20. Magyar A., Schönecker B., Wölfling J., Schneider G., Günther W., Görls H. Tetrahedron: Asymmetry. 14:2003;1925-1934.
21. Miljković D., Petrović J. J. Org. Chem. 42:1977;2101-2102.
22. Miljković D., Petrović J., Hadzic P. Tetrahedron. 34:1978;3575-3577.
23. Litvan F., Robinson R. J. Chem. Soc. 1938;1997-2001.
24. Frank É., Mernyák E., Wölfling J., Schneider G. Synlett. 2002;1803-1806.
25. Parish E.J., Aksara N., Boos T.L. Lipids. 32:1997;1325-1330.
26. Suggs J.W., Ytuarte L. Tetrahedron Lett. 27:1986;437-440.
27. Cohen K.F., Kazlauskas R., Pinhey J.T. J. Chem. Soc., Perkin Trans. 1. 1973;2076-2082.
28. Kusama H., Yamashita Y., Uchiyama K., Narasaka K. Bull. Chem. Soc. Jpn. 70:1997;965-975.
29. Miljković D., Penov-Gaši K., Djurendić E., Sakać M., Medić-Mijačević L., Pejanović V., Stanković S., Lazar D. Tetrahedron Lett. 38:1997;4683-4684.
30. Huffmann M. J. Biol. Chem. 167:1947;273-281.
31. Butenandt A., Schäffler E. Z. Naturforsch. 1:1946;82-87.
32. Ferrer J.C., Calzada V., Bonet J.J. Steroids. 55:1990;390-394.
33. Sheehan J.C., Coderre R.A., Cruickshank P.A. J. Am. Chem. Soc. 75:1953;6231-6233.
34. Arvidsson L., Johansson A.M., Hacksell U., Nilsson J.L.G., Svensson K., Hjorth S., Magnusson T., Carlsson A., Lindberg P., Andersson B., Sanches D., Wikström H., Sundell S. J. Med. Chem. 31:1988;92-99.
35. Back T.G., Lai E.K.Y., Morzycki J.W. Heterocycles. 32:1991;481-488.
36. Methoden der organischen Chemie (Houben-Weyl), 4. Auflage, Georg Thieme Verlag: Stuttgart, 1957, XI/1, pp. 863, 865, 953.
37. Hassner A., Lorber M.E., Heathcock C. J. Org. Chem. 32:1967;540-549.
38. COLLECT, Data Collection Software; Nonius BV, Netherlands, 1998.
39. Otwinowski, Z. & Minor, W. 'Processing of X-Ray Diffraction Data Collected in Oscillation Mode', In Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, Carter, C. W.; Sweet, R. M., Eds.; Academic Press: New York, 1997; pp. 307-326.
40. Sheldrick G.M. Acta Crystallogr., Sect. A. 46:1990;467-473.
41. Sheldrick, G. M. SHELXL-97 (Release 97-2), University of Göttingen, Germany, 1997.
42. CCDC 210986-210988 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 deposit@ccdc.cam.ac.uk).