Synthetic routes to 11-oxygenated 14α,17α-ethanoestradiols

European Journal of Organic Chemistry

Volumn , Issue 6, 2001, Pages 1189-1193

  Bull, James R ^a   De Koning, Pieter D ^b  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b ChiroTech Technology Ltd   (United Kingdom)

Author keywords

Epoxidations; Estradiol analogues; Hormones; Hydroborations; Steroids

Indexed keywords

11 OXO 14ALPHA,17ALPHA ETHANOESTRADIOL DERIVATIVE; ESTRADIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; EPOXIDATION; OXYGENATION;

EID: 0035086577     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200103)2001:6<1189::AID-EJOC1189>3.0.CO;2-H     Document Type: Article

References (21)

1. [1a] J. R. Bull, R. I. Thomson, H. Laurent, H. Schröder, R. Wiechert, Ger. Pat. DE 3 628 189, 1988 (Chem. Abstr. 1988, 109, 129451w). -
2. [1b] J. R. Bull, R. I. Thomson, J. Chem. Soc., Perkin Trans. 1 1990, 241-251.
3. [2a] G. Kirsch, G. Neef, H. Laurent, R. Wiechert, J. R. Bull, P. Esperling, W. Elger, S. Beier, Ger. Pat. DE 3 939 894, 1989 (Chem. Abstr. 1991, 115, 136493p). -
4. [2b] J. R. Bull, P. G. Mountford, G. Kirsch, G. Neef, A. Müller-Fahrnow, R. Wiechert, Tetrahedron 1994, 50, 6363-6376.
5. [3a] J. R. Bull, C. Hoadley, P. G. Mountford, L. M. Steer, J. Chem. Soc., Perkin Trans. 1 1997, 1179-1192. -
6. [3b] J. R. Bull, M. C. Loedolff, J. Chem. Soc., Perkin Trans. 1 1996, 1269-1276. -
7. [3c] J. R. Bull, P. G. Mountford, J. Chem. Soc., Perkin Trans. 1 1999, 1581-1587.
8. A. M. Brzozowski, A. C. W. Pike, Z. Dauter, R. E. Hubbard, T. Bonn, O. Engstrom, L. Ohman, G. L. Greene, J. A. Gustafsson, M. Carlquist, Nature 1997, 389, 753-758.
9. [5a] G. M. Anstead, K. E. Carlson, J. A. Katzenellenbogen, Steroids 1997, 62, 268-303. -
10. [5b] J. -M. Wurtz, U. Egner, N. Heinrich, D. Moras, A. Mueller-Fahrnow, J. Med. Chem. 1998, 41, 1803-1814. -
11. [5c] G. Gao, J. A. Katzenellenbogen, R. Garg, C. Hansch, Chem. Rev. 1999, 99, 723-744.
12. R. Tedesco, R. Fiaschi, E. Napolitano, J. Org. Chem. 1995, 60, 5316-5318 and references cited therein.
13. J. R. Bull, P. D. de Koning, J. Chem. Soc., Perkin Trans. 1 2000, 1003-1014.
14. D. J. Collins, J. Sjövall, Aust. J. Chem. 1983, 36, 339-360.
15. W. Adam, J. Bialas, L. Hadjiarapoglou, Chem. Ber. 1991, 124, 2377.
16. [10a] C. D. Liang, J. S. Baran, N. L. Allinger, Y. Yuh, Tetrahedron 1976, 32, 2067-2069. -
17. [10b] A. Segaloff, R. B. Gabbard, A. Flores, R. F. Borne, J. K. Baker, W. L. Duax, P. D. Strong, D. C. Rohrer, Steroids 1980, 35, 335-349.
18. K. Bischofberger, J. R. Bull, J. L. M. Dillen, P. H. van Rooyen, S. Afr. J. Chem. 1987, 40, 123-130.
19. [12a] D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156. -
20. [12b] R. E. Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899.
21. A. J. Mancuso, S. Huang, D. Swern, J. Org. Chem. 1978, 43, 2480-2482.