Cross-coupling Reactions for Steroid Modification: from Arylation to Macrocycle Syntheses

Lukashev, N.; Averin, A.; Latyshev, G.; Donez, P.; Ranyuk, E.; Beletskaya, I.

Artykuł - szczegóły

Tytuł artykułu

Cross-coupling Reactions for Steroid Modification: from Arylation to Macrocycle Syntheses

Autorzy

Lukashev N. , Averin A. , Latyshev G. , Donez P. , Ranyuk E. , Beletskaya I.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

The Suzuki-Miyaura coupling of 4- and 6-halosteroids affords good to excellent yields of potential aromatase inhibitors.While the reaction with 4- and 6-bromo derivatives is catalyzed by Pd(PPh3)2Cl2, the coupling with 6-chloro steroid (chlormadinone acetate) requires the use of Pd(dppb)Cl2 or Pd(dppf)Cl2. The palladium-catalyzed amination of bis(3-bromophenyl) ether of (5_)-cholane-3,24-diol with different polyamines leads to new macrocycles comprising one steroid and one polyamine fragments. Possibility of synthesis of macrocyclodimers containing two steroid and two polyamine fragments have been investigated.

Słowa kluczowe

cross-coupling palladium nickel steroids chlormadinone acetate Suzuki reaction litocholic acid polyamines macrocycles catalysis

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2006

Tom

Vol. 80, nr 4

Strony

559--572

Opis fizyczny

Bibliogr. 35 poz.

Twórcy

autor

Lukashev N.

autor

Averin A.

autor

Latyshev G.

autor

Donez P.

autor

Ranyuk E.

autor

Beletskaya I.

The Department of Chemistry, Moscow State Lomonosov University, 119992, Moscow, Russia

Bibliografia

1. Skoda-Foldes R. and Kollar L., Chem. Rev., 103, 4095 (2003).
2. Przezdziecka A., Kurek-Tyrlik A. and Wicha J., Collect. Czech. Chem. Commun., 67, 1658 (2002).
3. Arcadi A., Burini A., Cacchi S., Delmastro M., Marinelli F. and Pietroni B., Synlett, 47 (1990).
4. Gravett E.C., Hilton J.P., Jones K. and Romero F., Tetrahedron Lett., 42, 9081 (2001).
5. Cleve A,, Neef G., Ottów E., Scholz S. and Schwede W., Tetrahedron, 51, 5563 (1995).
6. Tuozzi A., Lo Sterzo C., Sperandio A. and Bocelli G., Tetrahedron, 55, 461 (1999).
7. Liu Z. and Meinwald J., J. Org. Chem., 61, 6693 (1996).
8. Stang P.J. and Treptow W., Synthesis, 283 (1984).
9. Barton D.H.R., Bashiardes G. and Fourrey J., Tetrahedron, 44, 147 (1988).
10. Levina I.S., Russ. Chem. Rev., 67, 975 (1998).
11. Lake D.E. and Hudis C., Cancer Control, 9, 490 (2002).
12. Brodie A.M.H., J. Steroid B lochem., 49, 281 (1994).
13. Suzuki A.J., J. Organomet. Chem., 653, 83 (2002).
14. Miyaura N., Top. Curr. Chem., 219, 11 (2002).
15. Suzuki A.J., J. Organomet. Chem., 576, 147 (1999).
16. Miyaura N. and Suzuki A.J., Chem. Rev., 95, 2457 (1995).
17. Beletskaya I.P. and Cheprakov A.V., in: Meyer T.J. and McCleverty J.A. (Eds): Comprehensive Coordination Chemistry II, vol. 9 ; Elsevier, Amsterdam, 2004, p. 305.
18. Satoh N., Ishiyama T., Miyaura N. and Suzuki S., Bull. Chem. Soc. Jpn., 60, 3471 (1987).
19. Indolese A.F., Tetrahedron Lett., 38, 3513 (1997).
20. Hassan J., Sevignon M., Gozzi C., Schulz E. and Lemaire M., Chem. Rev., 102, 1359 (2002).
21. BeletskayaI.P.,TsvetkovA.V.,LatyshevG.V.and Lukashev N.V.,Russ. J.. Org. Chem.,39,1660(2003).
22. Davis R., Chem. Soc. Rev., 243 (1993).
23. Wallimann R, Marti T., Fuerer A. and Diederich R, Chem. Rev., 97, 1567 (1997).
24. Li Y. and Dias J.R., Chem. Rev., 97, 283 (1997).
25. Virtanen E. and Kolehmainen E., Eur. J. Org. Chem., 3385 (2004).
26. Kolehmainen E., Tamminen J., Lappalainen K., Torkkel T. and Seppala R., Synthesis, 1082 (1996).
27. Tamminen J., Kolehmainen E., Haapala M. and Linnato J., Synthesis, 1464 (2000).
28. Ra S., Cho S.W. and Choi J.W., Buli. Korean Chem. Soc., 21, 342 (2000).
29. Maitra U., D'Souza L.J. and Kumar RV., Supramol. Chem., 10, 97 (1998).
30. Nair V., Prabhakaran J. and Eigendorf G.K., Synth. Commun., 27, 3095 (1997).
31. Beletskaya R, Averin A.D., Borisenko A.A., Denat F. and Guilard R., Tetrahedron Lett., 44, 1433 (2003).
32. Beletskaya R, Averin A.D., Pleshkova N.A., Borisenko A.A., SerebryakovaM.V., Denat F. and Guilard R., Synlett, 87 (2005).
33. Beletskaya R, Averin A.D., Bessmertnykh A.G., Denat F. and Guilard R., Eur. J. Org. Chem., 281 (2005).
34. Yang H. and Bucwald S.L., J. Organomet. Chem., 576, 125 (1999).
35. Wolfe J.R and Buchwald S.L., J. Org. Chem., 65, 1144 (2000).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ3-0006-0054