Synthesis of 15β-hydroxyalkyl-substituted (17Z)-pregn-17-enes, their ethers and esters

Russian Journal of Organic Chemistry

Volumn 40, Issue 11, 2004, Pages 1608-1616

  Baranovskii, A V ^a   Litvinovskaya, R P ^a   Khripach, V A ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

[No Author keywords available]

Indexed keywords

15BETA (4 ACETOXYBUTYL) 3ALPHA,5 CYCLO 5ALPHA PREGN 17 ENONE; 15BETA (4 ACETOXYBUTYL)PREGNA 2,16 DIENE 6 ONE; 15BETA (4 ACETOXYBUTYL)PREGNA 2,17 DIENE 6 ONE; 15BETA [4 (TETRAHYDROPYRAN 2 YLOXY)BUTYL] 3ALPHA,5 CYCLO 5ALPHA PREGN 17 EN 6 ONE; 3BETA (TERT BUTYLDIMETHYLSILYLOXY) 15BETA (4 HYDROXYBUTYL)PREGNA 5,17 DIENE; 3BETA (TERT BUTYLDIMETHYLSILYLOXY) 15BETA (4 PENTENYL)PREGNA 5,17 DIENE; 3BETA (TERT BUTYLDIMETHYLSILYLOXY) 15BETA (4 PIVALOYLOXYBUTYL)PREGNA 5,17 DIENE; 3BETA (TERT BUTYLDIMETHYLSILYLOXY) 15BETA [(4 TERT BUTYLSILYLDIMETHYLOXY) BUTYL]PREGNA 5,17 DIENE; 3BETA (TERT BUTYLDIMETHYLSILYLOXY) 15BETA [4 (TETRAHYDROPYRAN 2 YLOXY)BUTYL]PREGNA 5,17 DIENE; 3BETA HYDROXY 15BETA [4 (TETRAHYDROPYRAN 2 YLOXY)BUTYL]PREGNA 5,17 DIENE; ALKENYL GROUP; COPPER; ESTER DERIVATIVE; ETHER DERIVATIVE; OXOSTEROID; PREGNANE DERIVATIVE; REAGENT; STEROID; TERT BUTYLDIMETHYLSILYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; GRIGNARD REACTION; MOLECULE; SYNTHESIS; WITTIG REACTION;

EID: 18744394622     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11178-005-0067-4     Document Type: Article

References (29)

1. Mikami, K., Kishino, H., and Loh, T.P., Chem. Commun., 1994, p. 495.
2. Hazra, B.G., Pore, V.S., and Joshi, P.L., J. Chem. Soc., Perkin, Trans, I, 1993, p. 1819.
3. Houston, T.A., Tanaka, Y., and Koreeda, M., J. Org. Chem., 1993, vol. 58, p. 4287.
4. Mikami, K., Loh, T., and Nakai, T., Tetrahedron Asymmetry., 1990, vol. 1, p. 13.
5. Liu, D., Stuhmiller, L.M., and McMorris, T.C., J. Chem. Soc., Perkin, Trans. I, 1988, p. 2161.
6. Corey, E.J. and Venkateswarlu, A., J. Am. Chem. Soc., 1972, vol. 94, p. 6190.
7. Bull, J.R. and Loedolff, M., J. Chem. Soc., Perkin Trans. I, 1996, p. 1269.
8. Mongelli, N., Andreoni, A., Zuliani, L, and Gandolfi, C.A., Tetrahedron Lett., 1983, vol. 24, p. 3527.
9. Luppa, P., Hauck, S., Schwab, I., Birkmayer, C., and Hauptmann, H., Bioconjugate Chem., 1996, vol. 7, p. 332.
10. Schmuff, N.R. and Trost, B.M., J. Org. Chem., 1983, vol. 48, p. 1404.
11. Adamczyk, Y.Y., Chen, D.D., and Johnson, R.E., Tetrahedron, 1997. vol. 53, p. 12855.
12. Yamamoto, K., Ogura, H., Jukuta, J., Inoue, H., Hamada, K., Sugiyama, Y., and Yamada, S., J. Org. Chem., 1998, vol. 63, p. 4449.
13. Bojack, G. and Kunzer, H., Tetrahedron Lett., 1994, vol. 35, p. 9025.
14. Kihira, K. and Hoshita, T., Steroids, 1985, vol. 46, p. 767.
15. Katoch, R., Korde, S.S., Deodhar, K.D., and Trivedi, G.K., Tetrahedron, 1999, vol. 55, p. 1741.
16. Yang, D. and Zhang, C., J. Org. Chem., 2001, vol. 66, p. 4814.
17. Corey, E.J. and Wood, H.B., J. Am. Chem. Soc., 1996, vol. 118, p. 11982.
18. Hill, J., Sutherland, J.K., and Crowley, P., J. Chem. Soc., Perkin, Trans. I, 1992, p. 969.
19. Krishnamurthy, S., J. Org. Chem., 1981, vol. 46, p. 4628.
20. Vedejs, E., Cabaj, J., and Peterson, M.J., J. Org. Chem., 1993, vol. 58, p. 6509.
21. Trost, B.M. and Verhoeven, T.R., J. Org. Chem., 1976, vol. 41, p. 3416.
22. Shen, Y. and Burgoyne, D.L., J. Org. Chem., 2002, vol. 67, p. 3908.
23. Shull, B.K. and Koreeda, M., J. Org. Chem., 1990, vol. 55, p. 99.
24. Khripach, V.A., Zhabinskii, V.N., and de Groot, A., Brassinosteroids: A New Class of Plant Hormones, Academic Press, 1999, 456 p.
25. Sakurai, A., Yokota, T., and Clouse, S.D., Brassinosteroids: Steroidal Plant Hormones, Tokyo: Springer, Verlag, 1999, 253 p.
26. Anastasia, M., Allevi, P., Ciuffreda, P., and Oleotti, A., Steroids, 1985, vol. 45, p. 561.
27. Tavares, M., Ramasseul, R., Marchon, J.C., Vallee-Goyet, D., andGramain, J.C., J. Chem. Res. Synop., 1994, p. 74.
28. Perrin, D.D. and Armarego, W.L.F., Purification of Laboratory Chemicals, Oxford: Pergamon, Press, 1988, 391 p.
29. Takahashi, T., Ootake, A., Tsuji, J., and Tachibana, K., Tetrahedron, 1985, vol. 41, p. 5747.