Synthesis of C-C bonded dimeric steroids by olefin metathesis

Tetrahedron

Volumn 65, Issue 18, 2009, Pages 3615-3623

  Edelsztein, Valeria C ^a   Di Chenna, Pablo H ^a   Burton, Gerardo ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Dimeric steroids; Dimerization; Metathesis; Microwave

Indexed keywords

ALKENE; DEOXYCHOLIC ACID; ISOMERASE; PREGNENOLONE; PROGESTERONE; STEROID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIMERIZATION; HYDROGEN BOND; MICROWAVE COOKING; PRIORITY JOURNAL; RING CLOSING METATHESIS; SYNTHESIS;

EID: 63049119797     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.006     Document Type: Article

References (30)

1. Clemons P.A. Curr. Opin. Chem. Biol. 3 (1999) 112-115
2. Diver S.T., and Schreiber S.L. J. Am. Chem. Soc. 119 (1997) 5106-5109
3. Nicolaou K.C., Hughes R., Cho S.Y., Wissinger N., Smethurst C., and Enderman R. Angew. Chem., Int. Ed. 39 (2000) 3823-3828
4. For reviews on dimeric steroids see:. Nahar L., and Turner A.B. Curr. Med. Chem. 14 (2007) 1349-1370 and
5. Li Y.X., and Dias J.R. Chem. Rev. 97 (1997) 283-304
6. Mc Kenna J., Mc Kenna J.M., and Thornthwaite D.W. J. Chem. Soc., Chem. Commun. (1977) 809-811
7. Hoffman S., and Kumpf W. Z. Chem. 8 (1986) 293-295
8. López-Antón N., Rudy A., Barth N., Schmitz L.M., Pettit G.R., Schulze-Osthoff K., Dirsch V.M., and Vollmar A.M. J. Biol. Chem. 281 (2006) 33078-33086
9. Opsenica D., Pocsfalvi G., Juramic Z., Tinant B., Declercq J.-P., Kyle D.E., Milhous W.K., and Šolaja B.A. J. Med. Chem. 43 (2000) 3274-3282
10. Gouin S., and Zhu X.X. Langmuir 14 (1998) 4025-4029
11. Harmatha J., Budesinsky M., and Vokac k. Steroids 67 (2002) 127-135
12. Janout V., Jing B.W., and Regent S.L. Bioconjugate Chem. 13 (2002) 351-356
13. Pandey P.S., Rai R., and Singh R.B. J. Chem. Soc., Perkin Trans. 1 (2002) 918-923
14. Guthrie J.P., Cossar J., and Darson B.A. Can. J. Chem. 64 (1986) 2456-2469
15. Templeton J.F., Majgier-Baranowska H., and Marat K. Steroids 65 (2000) 219-223
16. DellaGreca M., Iesce M.R., Previtera L., Tamussi F., and Zarrelli A. J. Org. Chem. 67 (2002) 9011-9015
17. Morzycki J.W., Kalinowski S., Lotowski Z., and Rabiczko J. Tetrahedron 57 (1997) 10579-10590
18. Di Chenna P.H., Veleiro A.S., Sonego J.M., Ceballos N.R., Garland M.T., Baggio R.F., and Burton G. Org. Biomol. Chem. 5 (2007) 2453-2457
19. Veleiro A.S., Taich P.J., Alvarez L.D., Di Chenna P.H., and Burton G. Tetrahedron Lett. 46 (2005) 4235-4238
20. Grubbs R.H. Tetrahedron 60 (2004) 7117-7140
21. Bérubé M., and Poirier D. Org. Lett. 6 (2004) 3127-3130
22. Rega M., Jiménez C., and Rodríguez J. Steroids 72 (2007) 729-735
23. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360-11370
24. Bargiggia F.C., and Murray W.V. J. Org. Chem. 70 (2005) 9636-9639
25. Concepción J.I., Francisco C.G., Freire R., Hernandez R., Salazar J.A., and Suarez E. J. Org. Chem. 51 (1986) 402-404
26. Tochtrop G.P., DeKoster G.T., Cistola D.P., and Covey D.F. Bioorg. Med. Chem. 12 (2002) 433-435
27. Fajkos J., and Josca J. Collect. Czech. Chem. Commun. 44 (1979) 251-258
28. Joselevich M., Ghini A.A., and Burton G. Org. Biomol. Chem. 1 (2003) 939-943
29. In: Hill R.A., Kirk D.N., Makin H.L., and Murphy G.M. (Eds). Dictionary of Steroids: Chemical Data, Structures and Bibliographies (1991), Chapman & Hall, Cambridge, Great Britain
30. Aburatani N., Takeuchi T., and Mori K. Synthesis (1987) 181-183