Novel medium ring sized estradiol derivatives by intramolecular Heck reactions

Synlett

Volumn , Issue 10, 2003, Pages 1494-1496

  Tietze, Lutz F ^a   Sommer, Konrad M ^a   Schneider, Gyula ^b   Tapolcsányi, Pál ^b   Wölfling, János ^b   Müller, Peter ^a   Noltemeyer, Mathias ^a   Terlau, Heinrich ^c  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF SZEGED   (Hungary)

^c MAX PLANCK INSTITUTE OF EXPERIMENTAL MEDICINE   (Germany)

Author keywords

Carbocycles; Estradiol derivatives; Grignard reactions; Heck reaction; Steroids

Indexed keywords

ESTRADIOL DERIVATIVE; ESTRONE DERIVATIVE;

ARTICLE; ESTROGEN SYNTHESIS; GRIGNARD REACTION; HECK REACTION; MOLECULAR SIZE; REACTION ANALYSIS;

EID: 0043071416     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40832     Document Type: Article

References (28)

1. For an overview of the Heck reaction see: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (b) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 99-166; and references cited therein.
2. For an overview of the Heck reaction see: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (b) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 99-166; and references cited therein.
3. (a) Tietze, L. F.; Nöbel, T.; Spescha, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259; Angew. Chem. 1996, 108, 2385.
4. (a) Tietze, L. F.; Nöbel, T.; Spescha, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259; Angew. Chem. 1996, 108, 2385.
5. (b) Tietze, L. F.; Nöbel, T.; Spescha, M. J. Am. Chem. Soc. 1998, 120, 8971.
6. (c) Tietze, L. F.; Petersen, S. Eur. J. Org. Chem. 2000, 1827.
7. (d) Tietze, L. F.; Ferraccioli, R. Synlett 1998, 145.
8. (e) Tietze, L. F.; Petersen, S. Eur. J. Org. Chem. 2001, 1619.
9. Schneider, G.; Bottka, S.; Hackler, L.; Wölfling, J.; Sohár, P. Liebigs Ann. Chem. 1989, 263.
10. Yokoyama, Y.; Matsushima, H.; Takashima, M.; Suzuki, T.; Murakami, Y. Heterocycles 1997, 46, 133.
11. Piers, E.; Oballa, R. M. Tetrahedron Lett. 1995, 36, 5857.
12. Masters, J. J.; Jung, D. K.; Bornmann, W. G.; Danishefsky, S. J.; de Gala, S. Tetrahedron Lett. 1993, 34, 7253.
13. Kwon, O.; Su, D.; Meng, O.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem. Int. Ed. 1998, 37, 1880; Angew. Chem. 1998, 110, 1981.
14. Kwon, O.; Su, D.; Meng, O.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem. Int. Ed. 1998, 37, 1880; Angew. Chem. 1998, 110, 1981.
15. Ma, S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
16. Joung, W. B.; Masters, J. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5228.
17. Gibson, S. E.; Middleton, R. J. J. Chem. Soc., Chem. Commun. 1995, 1743.
18. Beeby, M. H.; Mann, F. G. J. Chem. Soc. 1951, 411.
19. Joyeau, R.; Yadav, L. D. S.; Wakselman, M. J. Chem. Soc., Perkin Trans. 1 1987, 1899.
20. Ang, H. G.; Chang, B.; Kwik, W. L.; Sim, E. S. H. J. Organomet. Chem. 1994, 474, 153.
21. Barkov, A.; Grützmacher, H. F. Int. J. Mass Spectrom. Ion Processes 1995, 142, 195.
22. Iambushev, F. D.; Kokorev, G. I.; Khalimov, F. G. Zh. Obshch. Khim. 1984, 54, 2005.
23. Herrmann, W. A.; Broßmer, C.; Öfele, K.; Reisinger, C. P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; Angew. Chem. 1995, 107, 1989.
24. Herrmann, W. A.; Broßmer, C.; Öfele, K.; Reisinger, C. P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; Angew. Chem. 1995, 107, 1989.
25. Horwell, D. C.; Nichols, P. D.; Ratcliffe, G. S.; Roberts, E. J. Org. Chem. 1994, 59, 4418.
26. 3), 111.7 (C-2), 113.4 (C-4), 120.7 (C-16a), 126.2, 126.5, 127.1, 129.0, 130.2, 132.0 (C-10), 134.0, 137.7 (C-5), 141.1, 147.4 (C-16), 157.7 (C-3), 215.3 (C-17c).
27. Crystallographic data for 4 and 20 can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Deposition numbers: CCDC 168413 for 4 and CCDC 168412 for 20.
28. 3O), 73.6 (C-17d), 111. 6 (C-2), 113.5 (C-4), 126.3, 126.6, 126.9 (2C), 127.1, 131.4, 133.0 (C-10), 135.7, 136.2, 137.3, 138.1 (C-5), 157.5 (C-3).