Access to 11β-ethynyl-androst-5-ene

Tetrahedron Letters

Volumn 46, Issue 7, 2005, Pages 1123-1126

  Lecomte, Vincent ^a   Stéphan, Elie ^b   Jaouen, Gérard ^b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

Alkynes; Radical reactions; Steroids

Indexed keywords

11BETA ETHYNYLANDROST 5 ENE; ADRENOSTERONE; OXALIC ACID; STEROID; UNCLASSIFIED DRUG;

ARTICLE; DEOXYGENATION; DRUG SYNTHESIS; QUANTUM YIELD;

EID: 12344311334     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.082     Document Type: Article

References (24)

1. M.P. Sibi, and N.A. Porter Acc. Chem. Res. 32 1999 163 171
2. A.J. Buckmelter, J.P. Powers, and S.D. Rychnovsky J. Am. Chem. Soc. 120 1998 5589 5590
3. S.C. Dolan, and J. McMillan J. Chem. Soc., Chem. Comm. 1985 1588 1589
4. V. Lecomte, E. Stéphan, M.N. Rager, and G. Jaouen J. Org. Chem. 69 2004 3216 3219
5. A. Cleve, K.-H. Fritzemeier, N. Heinrich, U. Klar, A. Müller-Fahrnow, G. Neef, E. Ottow, and W. Schwede Tetrahedron 52 1996 1529 1542
6. See also, for modification of the symmetrical position 7, Y. Zheng, and Y. Li J. Org. Chem. 68 2003 1603 1606
7. 13C NMR
8. D. Griller, K.U. Ingold, P.J. Krusic, and H. Fischer J. Am. Chem. Soc. 100 1978 6750 6752
9. J.H. Babler, V.P. Liptak, and N. Phan J. Org. Chem. 61 1996 416 417
10. D. Tzalis, and P. Knochel Angew. Chem., Int. Ed. 38 1999 1463 1465
11. D.E. Frantz, R. Fässler, and E.M. Carreira J. Am. Chem. Soc. 122 2000 1806 1807
12. T. Ishikawa, T. Mizuta, K. Hagiwara, T. Aikawa, T. Kudo, and S. Saito J. Org. Chem. 68 2003 3702 3705
13. J.A. Zderic, E. Batres, D. Chavez Limon, H. Carpio, J. Lisci, G. Monroy, E. Necoechea, and H.J. Ringold J. Am. Chem. Soc. 82 1960 3404 3409
14. V. Lecomte, E. Stéphan, and G. Jaouen Tetrahedron 59 2003 2169 2176
15. J.E. Bridgeman, P.C. Cherry, A.S. Clegg, J.M. Avans, E.R.H. Sir Jones, A. Kasal, V. Kumar, G.D. Meakins, Y. Morisawa, E.E. Richards, and P.D. Woodgate J. Chem. Soc. (C) 1970 250 257
16. V. Lecomte, N. Foy, F. Le Bideau, E. Stéphan, and G. Jaouen Tetrahedron Lett. 42 2001 5409 5411
17. In the steroid series: C.W. Shoppee, and R.E. Lack J. Chem. Soc. 1962 3624 3629
18. G. Teutsch, G. Costerousse, R. Deraedt, J. Benzoni, M. Fortin, and D. Philibert Steroids 38 1981 651 665
19. W. Chodkiewicz Ann. Chim. 11 1957 819 852
20. -1) 2953, 2878, 1771, 1751
21. +] (4), 99 (100)
22. +] (100)
23. +] (100)
24. 3): δ (ppm) 16.0, 20.4, 22.8, 24.9, 29.8, 30.8, 31.4, 34.1, 35.4, 37.0, 37.4, 40.8, 45.7, 51.7, 52.6, 64.2, 64.4, 64.5, 65.1, 72.6, 90.3, 109.1 (C-3), 119.4 (C-17), 120.7 (C-6), 141.2 (C-5)