Synthesis of enantiopure B-nor-steroids by multiple Pd-catalyzed transformations

Journal of Organometallic Chemistry

Volumn 687, Issue 2, 2003, Pages 346-352

  Tietze, Lutz F ^a   Wiegand, J Matthias ^a   Vock, Carsten ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

B nor estradiol; Heck reaction; Microwave; Palladium; Steroids; Suzuki reaction

Indexed keywords

BENZYL CHLORIDE; BORONIC ACID DERIVATIVE; BROMINE DERIVATIVE; ESTRADIOL; ESTROGEN; KETONE DERIVATIVE; PALLADIUM; STEROID;

ARTICLE; BETA CHAIN; CELL SURFACE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG BINDING; DRUG DESIGN; DRUG SYNTHESIS; ENANTIOMER; ENDOTHELIUM; HECK REACTION; HIGH TEMPERATURE PROCEDURES; HORMONE ACTION; MICROWAVE IRRADIATION; POTASSIUM CHANNEL;

LATEOLABRAX JAPONICUS;

EID: 0344012098     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(03)00720-4     Document Type: Article

References (47)

1. Bräse S. de Meijere A., in: Negishi E.-I. (Ed.), Handbook of Organopalladium Chemistry for Organic Synthesis 1 2002 1179-1208 Wiley Hoboken
2. Beletskaya I.P. Cheprakov A.V. Chem. Rev. 100 2000 3009
3. Shibasaki M. Boden C.D.J. Kojima A. Tetrahedron 53 1997 7371
4. Tietze L.F. Haunert F. in: Shibasaki M. Stoddart J.F. Vögtle F. (Eds.), Stimulating Concepts in Chemistry 2000 39-64 Wiley-VCH Weinheim
5. Tietze L.F. Chem. Rev. 96 1996 115
6. Tietze L.F. Beifuss U. Angew. Chem. 105 1993 137
7. Tietze L.F. Beifuss U. Angew. Chem. Int. Ed. Engl. 32 1993 131
8. Tietze L.F. Nordmann G. Eur. J. Org. Chem. 2001 3247
9. Tietze L.F. Schirok H. Wöhrmann M. Schrader K. Eur. J. Org. Chem. 2000 2433
10. Tietze L.F. Schirok H. Wöhrmann M. Chem. Eur. J. 6 2000 510
11. Tietze L.F. Schirok H. J. Am. Chem. Soc. 121 1999 10264
12. Tietze L.F. Schirok H. Angew. Chem. 109 1997 1159
13. Tietze L.F. Schirok H. Angew. Chem. Int. Ed. Engl. 36 1997 1124
14. Tietze L.F. Petersen S. Eur. J. Org. Chem. 2001 1619
15. Tietze L.F. Petersen S. Eur. J. Org. Chem. 2000 1827
16. Tietze L.F. Nöbel T. Spescha M. J. Am. Chem. Soc. 35 1998 8971
17. Tietze L.F. Nöbel T. Spescha M. Angew. Chem. 108 1996 2385
18. Tietze L.F. Nöbel T. Spescha M. Angew. Chem. Int. Ed. Engl. 35 1996 2259
19. Herrmann W.A. Böhm V.P.W. Reisinger C.-P. J. Organomet. Chem. 576 1999 23
20. Beller M. Fischer H. Herrmann W.A. Öfele K. Broßmer C. Angew. Chem. 107 1995 1992
21. Beller M. Fischer H. Herrmann W.A. Öfele K. Broßmer C. Angew. Chem. Int. Ed. Engl. 34 1995 1848
22. Herrmann W.A. Broßmer C. Öfele K. Reisinger C.-P. Priermeier T. Beller M. Fischer H. Angew. Chem. 107 1995 1989
23. Herrmann W.A. Broßmer C. Öfele K. Reisinger C.-P. Priermeier T. Beller M. Fischer H. Angew. Chem. Int. Ed. Engl. 34 1995 1844
24. Valverde M.A. Rojas P. Amigo J. Cosmelli D. Orio P. Bahamonde M.I. Mann G.E. Vergara C. Latorre R. Science 285 5435 1999 1929
25. L.F. Tietze, K. Sommer, C. Vock, J.M. Wiegand, unpublished results.
26. Shavva A.G. Selivanov S.I. Starova G.L. Boronoeva T.R. Ishchenko I.V. Gluzdikov I.A. Sharetskii A.N. Isaeva V.G. Surinov B.P. Russ. J. Bioorg. Chem. 28 2002 215
27. Ischenko I.V. Shavva A.G. Russ. J. Org. Chem. 28 1992 178
28. Shavva A.G. Eliseev I.I. Burova E.B. Kovalchuk S.V. Gindin V.A. Russ. J. Org. Chem. 22 1986 391
29. Kasturi T.R. Parvathi S. J. Chem. Soc. Perkin Trans. 1 1980 448
30. Ila H. Dabral V. Anand N. Indian J. Chem. 12 1974 543
31. Rufer C. Liebigs Ann. Chem. 717 1968 228
32. Heidepriem H. Rufer C. Kosmol H. Schroeder E. Kieslich K. Liebigs Ann. Chem. 712 1968 155
33. Burckhalter J.H. Sciavolino F.C. J. Org. Chem. 32 1967 3968
34. Song Z.J. Zhao M. Desmond R. Devine P. Tschaen D.M. Tillyer R. Frey L. Heid R. Xu F. Foster B. Li J. Reamer R. Volante R. Grabowski E.J.J. Dolling U.H. Reider P.J. Okada S. Kato Y. Mano E. J. Org. Chem. 64 1999 9658
35. Gardner J.H. McDonnell T.F. J. Am. Chem. Soc. 63 1941 2279
36. Dams M. Drijkoningen L. De Vos D. Jacobs P. Chem. Commun. 2002 1062
37. Wang L. Pan Y. Jiang X. Hu H. Tetrahedron Lett. 41 2000 725
38. Kumar P. Org. Prep. Proced. Int. 29 1997 477
39. Yi P. Zhuangyu Z. Hu H. Synth. Commun. 22 1992 2019
40. Hashem M.A. Weyerstahl P. Tetrahedron 40 1984 2003
41. Micheli R.A. Hajos Z.G. Cohen N. Parrish D.R. Portland L.A. Sciamanna W. Scott M.A. Wehrli P.A. J. Org. Chem. 40 1975 675
42. Eder U. Sauer G. Wiechert R. Angew. Chem. 83 1971 492
43. Eder U. Sauer G. Wiechert R. Angew. Chem. Int. Ed. Engl. 10 1971 496
44. Luche J.-L. Rodriguez-Hahn L. Crabbe P. J. Chem. Soc. Chem. Commun. 1978 601
45. Bose A.K. Manhas M.S. Ganguly S.N. Sharma A.H. Banik B.K. Synthesis 11 2002 1579
46. Lindström P. Tierny J. Wathey B. Westman J. Tetrahedron 57 2001 9225
47. Caddick S. Tetrahedron 51 1995 10403