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Chemistry - A European Journal

Volumn 18, Issue 18, 2012, Pages 5515-5518

Synthesis of ferrocenestrone: The first metallocene based steroid analogue

(5) Hessler, Filip a Císařová, Ivana a Sedlák, David b Bartůněk, Petr b Kotora, Martin a,c

a CHARLES UNIVERSITY (Czech Republic)

b INSTITUTE OF MOLECULAR GENETICS (Czech Republic)

c INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY (Czech Republic)

Author keywords

asymmetric synthesis; ferrocenestrones; metallocenes; steroids; synthesis design

Indexed keywords

ASYMMETRIC SYNTHESIS; DIELS-ALDER REACTION; DOUBLE BONDS; ENANTIOSELECTIVE; ENYNE METATHESIS; FERROCENES; FERROCENESTRONES; FUNCTIONALIZATIONS; SIDE-CHAINS; STEROIDS; SYNTHESIS DESIGN;

IRON COMPOUNDS;

ORGANOMETALLICS;

FERROCENE; FERROUS ION; METALLOCENE; ORGANOMETALLIC COMPOUND; STEROID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CHEMISTRY TECHNIQUES, SYNTHETIC; CRYSTALLOGRAPHY, X-RAY; FERROUS COMPOUNDS; HYDROGENATION; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; STEROIDS;

EID: 84859902880 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201200687 Document Type: Article

Times cited : (13)

References (49)

1
- 11144333768
- D. R. van Staveren, N. Metzler-Nolte, Chem. Rev. 2004, 104, 5931-5985
- (2004) Chem. Rev. , vol.104 , pp. 5931-5985
- Van Staveren, D.R.¹ Metzler-Nolte, N.²

2
- 34547168018
- M. F. R. Fouda, M. M. Abd-Elzaher, R. A. Abdelsamaia, A. A. Labib, Appl. Organomet. Chem. 2007, 21, 613-625
- (2007) Appl. Organomet. Chem. , vol.21 , pp. 613-625
- Fouda, M.F.R.¹ Abd-Elzaher, M.M.² Abdelsamaia, R.A.³ Labib, A.A.⁴

3
- 77954852252
- T. Moriuchi, T. Hirao, Acc. Chem. Res. 2010, 43, 1040-1051.
- (2010) Acc. Chem. Res. , vol.43 , pp. 1040-1051
- Moriuchi, T.¹ Hirao, T.²

4
- 80051490261
- For a recent synthesis of ferrocene-containing HETE analogues, see
- For a recent synthesis of ferrocene-containing HETE analogues, see:, N. Kausch-Busies, J. M. Neudörfl, P. Wefelmeier, A. Prokop, H. Kühn, H.-G. Schmalz, Eur. J. Org. Chem. 2011, 4634-4644.
- (2011) Eur. J. Org. Chem. , pp. 4634-4644
- Kausch-Busies, N.¹ Neudörfl, J.M.² Wefelmeier, P.³ Prokop, A.⁴ Kühn, H.⁵ Schmalz, H.-G.⁶

5
- 0025040502
- A. VessiÄres, C. Vaillant, M. Gruselle, D. Vichard, G. Jaouen, J. Chem. Soc., Chem. Commun. 1990, 35, 837-838
- (1990) J. Chem. Soc., Chem. Commun. , vol.35 , pp. 837-838
- Vessiäres, A.¹ Vaillant, C.² Gruselle, M.³ Vichard, D.⁴ Jaouen, G.⁵

6
- 0026706764
- H. El Amouri, A. Vessieres, D. Vichard, S. Top, M. Gruselle, G. Jaouen, J. Med. Chem. 1992, 35, 3130-3135
- (1992) J. Med. Chem. , vol.35 , pp. 3130-3135
- El Amouri, H.¹ Vessieres, A.² Vichard, D.³ Top, S.⁴ Gruselle, M.⁵ Jaouen, G.⁶

7
- 0001849641
- D. Vichard, M. Gruselle, G. Jaouen, M. N. Nefedova, I. A. Mamedyarova, V. I. Sokolov, J. Vaissermann, J. Organomet. Chem. 1994, 484, 1-8
- (1994) J. Organomet. Chem. , vol.484 , pp. 1-8
- Vichard, D.¹ Gruselle, M.² Jaouen, G.³ Nefedova, M.N.⁴ Mamedyarova, I.A.⁵ Sokolov, V.I.⁶ Vaissermann, J.⁷

8
- 0000294811
- D. Osella, O. Gambino, G. C. Dutto, C. Nervi, G. Jaouenâ A. Vessieres, Inorg. Chim. Acta 1994, 218, 207-210
- (1994) Inorg. Chim. Acta , vol.218 , pp. 207-210
- Osella, D.¹ Gambino, O.² Dutto, G.C.³ Nervi, C.⁴ Vessieres, G.J.A.⁵

9
- 84859916782
- J. Tang, X.-G. Li, Youji Huaxue 1999, 19, 312-315
- (1999) Youji Huaxue , vol.19 , pp. 312-315
- Tang, J.¹ Li, X.-G.²

10
- 77952734111
- J. Manosroi, K. Rueanto, K. Boonpisuttinant, W. Manosroi, C. Biot, H. Akazawa, T. Akihisa, W. Issarangporn, A. Manosroi, J. Med. Chem. 2010, 53, 3937-3943.
- (2010) J. Med. Chem. , vol.53 , pp. 3937-3943
- Manosroi, J.¹ Rueanto, K.² Boonpisuttinant, K.³ Manosroi, W.⁴ Biot, C.⁵ Akazawa, H.⁶ Akihisa, T.⁷ Issarangporn, W.⁸ Manosroi, A.⁹

11
- 0000379460
- E. Winterfeldt, Chem. Rev. 1993, 93, 827-843
- (1993) Chem. Rev. , vol.93 , pp. 827-843
- Winterfeldt, E.¹

12
- 33745457515
- Y. Okada, S. Matsunaga, R. W. N. Van Soest, N. Fusetani, J. Org. Chem. 2006, 71, 4884-4888.
- (2006) J. Org. Chem. , vol.71 , pp. 4884-4888
- Okada, Y.¹ Matsunaga, S.² Van Soest, R.W.N.³ Fusetani, N.⁴

13
- 42649083642
- C. Tan, Y. Di, Y. Wang, Y. Wang, S. Mu, S. Gao, Y. Zhang, N. Kong, H. He, J. Zhang, X. Fang, C. Li, Y. Lu, X. Hao, Tetrahedron Lett. 2008, 49, 3376-3379.
- (2008) Tetrahedron Lett. , vol.49 , pp. 3376-3379
- Tan, C.¹ Di, Y.² Wang, Y.³ Wang, Y.⁴ Mu, S.⁵ Gao, S.⁶ Zhang, Y.⁷ Kong, N.⁸ He, H.⁹ Zhang, J.¹⁰ Fang, X.¹¹ Li, C.¹² Lu, Y.¹³ Hao, X.¹⁴

14
- 84985292976
- E. R. Biehl, P. C. Reeves, Synthesis 1973, 360-361
- (1973) Synthesis , pp. 360-361
- Biehl, E.R.¹ Reeves, P.C.²

15
- 0029934255
- C. J. Richards, A. W. Mulvaney, Tetrahedron: Asymmetry 1996, 7, 1419-1430
- (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1419-1430
- Richards, C.J.¹ Mulvaney, A.W.²

16
- 33751157112
- T. Sammakia, H. A. Latham, D. R. Schaad, J. Org. Chem. 1995, 60, 10-11
- (1995) J. Org. Chem. , vol.60 , pp. 10-11
- Sammakia, T.¹ Latham, H.A.² Schaad, D.R.³

17
- 3843120162
- R. Kuwano, T. Uemura, M. Saitoh, Y. Ito, Tetrahedron: Asymmetry 2004, 15, 2263-2271
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 2263-2271
- Kuwano, R.¹ Uemura, T.² Saitoh, M.³ Ito, Y.⁴

18
- 0034659865
- H. Plenio, J. Hermann, A. Sehring, Chem. Eur. J. 2000, 6, 1820-1829
- (2000) Chem. Eur. J. , vol.6 , pp. 1820-1829
- Plenio, H.¹ Hermann, J.² Sehring, A.³

19
- 38449108467
- J. Ma, M. Vollmann, H. Menzel, J. Inorg. Organomet. Polym. Zeitschrift wurde bereits 2004 stillgelegt! 2008, 18, 41-50.
- (2008) J. Inorg. Organomet. Polym. Zeitschrift Wurde Bereits 2004 Stillgelegt! , vol.18 , pp. 41-50
- Ma, J.¹ Vollmann, M.² Menzel, H.³

20
- 2342534957
- Y. Ikeuchi, T. Taguchi, Y. Hanzawa, Tetrahedron Lett. 2004, 45, 4495-4498
- (2004) Tetrahedron Lett. , vol.45 , pp. 4495-4498
- Ikeuchi, Y.¹ Taguchi, T.² Hanzawa, Y.³

21
- 0029147242
- Y. Hanzawa, Y. Ikeuchi, T. Nakamura, T. Taguchi, Tetrahedron Lett. 1995, 36, 6503-6506
- (1995) Tetrahedron Lett. , vol.36 , pp. 6503-6506
- Hanzawa, Y.¹ Ikeuchi, Y.² Nakamura, T.³ Taguchi, T.⁴

22
- 12344264552
- Y. Ikeuchi, T. Taguchi, Y. Hanzawa, J. Org. Chem. 2005, 70, 756-759.
- (2005) J. Org. Chem. , vol.70 , pp. 756-759
- Ikeuchi, Y.¹ Taguchi, T.² Hanzawa, Y.³

23
- 33645997033
- P. Herrmann, M. Kotora, M. Buděšínský, D. Åaman, I. CísaÅová, Org. Lett. 2006, 8, 1315-1318
- (2006) Org. Lett. , vol.8 , pp. 1315-1318
- Herrmann, P.¹ Kotora, M.² Buděšínskã, M.³ Åaman, D.⁴ Císařová, I.⁵

24
- 36049049302
- P. Herrmann, M. Buděšínský, M. Kotora, Chem. Lett. 2007, 36, 1268-1269
- (2007) Chem. Lett. , vol.36 , pp. 1268-1269
- Herrmann, P.¹ Buděšínskã, M.² Kotora, M.³

25
- 50149092636
- P. Herrmann, M. Buděšínský, M. Kotora, J. Org. Chem. 2008, 73, 6202-6206.
- (2008) J. Org. Chem. , vol.73 , pp. 6202-6206
- Herrmann, P.¹ Buděšínskã, M.² Kotora, M.³

26
- 0028145914
- T. Takahashi, M. Kotora, K. Kasai, N. Suzuki, Tetrahedron Lett. 1994, 35, 5685-5688
- (1994) Tetrahedron Lett. , vol.35 , pp. 5685-5688
- Takahashi, T.¹ Kotora, M.² Kasai, K.³ Suzuki, N.⁴

27
- 37049077025
- T. Takahashi, M. Kotora, Z. Xi, J. Chem. Soc. Chem. Commun. 1995, 1503-1504
- (1995) J. Chem. Soc. Chem. Commun. , pp. 1503-1504
- Takahashi, T.¹ Kotora, M.² Xi, Z.³

28
- 17744384463
- K. Kasai, M. Kotora, N. Suzuki, T. Takahashi, J. Chem. Soc. Chem. Commun. 1995, 109-110
- (1995) J. Chem. Soc. Chem. Commun. , pp. 109-110
- Kasai, K.¹ Kotora, M.² Suzuki, N.³ Takahashi, T.⁴

29
- 0003127759
- T. Takahashi, Y. Nishihara, R. Hara, S. Huo, M. Kotora, Chem. Commun. 1997, 1599-1600.
- (1997) Chem. Commun. , pp. 1599-1600
- Takahashi, T.¹ Nishihara, Y.² Hara, R.³ Huo, S.⁴ Kotora, M.⁵

30
- 78650910230
- E. Dane, J. Schmitt, Liebigs Ann.Chem. 1939, 537, 246-249.
- (1939) Liebigs Ann.Chem. , vol.537 , pp. 246-249
- Dane, E.¹ Schmitt, J.²

31
- 0006114926
- K. Tanaka, H. Nakashima, T. Taniguchi, K. Ogasawara, Org. Lett. 2000, 2, 1915-1917
- (2000) Org. Lett. , vol.2 , pp. 1915-1917
- Tanaka, K.¹ Nakashima, H.² Taniguchi, T.³ Ogasawara, K.⁴

32
- 0038666308
- S. B. Tsogoeva, G. Durner, M. Bolte, M. Gobel, Eur. J. Org. Chem. 2003, 1661
- (2003) Eur. J. Org. Chem. , pp. 1661
- Tsogoeva, S.B.¹ Durner, G.² Bolte, M.³ Gobel, M.⁴

33
- 2442536129
- Q.-Y. Hu, P. D. Rege, E. J. Corey, J. Am. Chem. Soc. 2004, 126, 5984-5986
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5984-5986
- Hu, Q.-Y.¹ Rege, P.D.² Corey, E.J.³

34
- 49649124668
- E. Canales, E. J. Corey, Org. Lett. 2008, 10, 3271-3273
- (2008) Org. Lett. , vol.10 , pp. 3271-3273
- Canales, E.¹ Corey, E.J.²

35
- 77950962949
- M. Weimar, G. Dürner, J. W. Bats, M. W. Gödel, J. Org. Chem. 2010, 75, 2718-2721.
- (2010) J. Org. Chem. , vol.75 , pp. 2718-2721
- Weimar, M.¹ Dürner, G.² Bats, J.W.³ Gödel, M.W.⁴

36
- 79956110782
- For G I catalyzed reactions, see:, For G II catalyzed reactions, see Ref. [8c]
- For G I catalyzed reactions, see:, M. E. Jung, D. Yoo, Org. Lett. 2011, 13, 2698-2701. For G II catalyzed reactions, see Ref. [8c].
- (2011) Org. Lett. , vol.13 , pp. 2698-2701
- Jung, M.E.¹ Yoo, D.²

37
- 0001525502
- N. Chatani, N. Furukawa, H. Sakurai, S. Murai, Organometallics 1996, 15, 901-903.
- (1996) Organometallics , vol.15 , pp. 901-903
- Chatani, N.¹ Furukawa, N.² Sakurai, H.³ Murai, S.⁴

38
- 0029094493
- G. Quinkert, M. Del Rosso, A. Döring, R. I. Schenkel, M. Bauch, G. T. Dambacher, J. W. Bats, G. Zimmermann, G. Dümer, Helv. Chim. Acta 1995, 78, 1345-1391.
- (1995) Helv. Chim. Acta , vol.78 , pp. 1345-1391
- Quinkert, G.¹ Del Rosso, M.² Döring, A.³ Schenkel, R.I.⁴ Bauch, M.⁵ Dambacher, G.T.⁶ Bats, J.W.⁷ Zimmermann, G.⁸ Dümer, G.⁹

39
- 0022632271
- G. H. Posner, C. Switzer, J. Am. Chem. Soc. 1986, 108, 1239-1244.
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 1239-1244
- Posner, G.H.¹ Switzer, C.²

40
- 33746713756
- C. Lim, G. N. Evenson, W. R. Perrault, B. A. Pearlman, Tetrahedron Lett. 2006, 47, 6417-6420.
- (2006) Tetrahedron Lett. , vol.47 , pp. 6417-6420
- Lim, C.¹ Evenson, G.N.² Perrault, W.R.³ Pearlman, B.A.⁴

41
- 33845374498
- R. H. Crabtree, M. W. Davies, J. Org. Chem. 1986, 51, 2655-2661
- (1986) J. Org. Chem. , vol.51 , pp. 2655-2661
- Crabtree, R.H.¹ Davies, M.W.²

42
- 34250657376
- Z. Song, R. P. Hsung, Org. Lett. 2007, 9, 2199-2202.
- (2007) Org. Lett. , vol.9 , pp. 2199-2202
- Song, Z.¹ Hsung, R.P.²

43
- 0030092911
- M. Sakakibara, A. O. Uchida, Biosci. Biotechnol. Biochem. 1996, 60, 405-414.
- (1996) Biosci. Biotechnol. Biochem. , vol.60 , pp. 405-414
- Sakakibara, M.¹ Uchida, A.O.²

44
- 33746494993
- Y. Ito, T. Hirao, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013.
- (1978) J. Org. Chem. , vol.43 , pp. 1011-1013
- Ito, Y.¹ Hirao, T.² Saegusa, T.³

45
- 3042817163
- V. A. Khripach, V. N. Zhabinski, G. P. Fando, A. I. Kuchto, A. S. Lyakhov, A. A. Govorova, M. B. Groen, J. van der Louw, A. de Groot, Steroids 2004, 69, 495-499.
- (2004) Steroids , vol.69 , pp. 495-499
- Khripach, V.A.¹ Zhabinski, V.N.² Fando, G.P.³ Kuchto, A.I.⁴ Lyakhov, A.S.⁵ Govorova, A.A.⁶ Groen, M.B.⁷ Van Der Louw, J.⁸ De Groot, A.⁹

46
- 29144464906
- T. P. Brady, S. H. Kim, K. Wen, C. Rim, E. A. Theodorakis, Chem. Eur. J. 2005, 11, 7175-7190.
- (2005) Chem. Eur. J. , vol.11 , pp. 7175-7190
- Brady, T.P.¹ Kim, S.H.² Wen, K.³ Rim, C.⁴ Theodorakis, E.A.⁵

47
- 79953315985
- D. Sedlak, A. Paguio, P. Bartunek, Comb. Chem. High Throughput Screening 2011, 14, 248-266.
- (2011) Comb. Chem. High Throughput Screening , vol.14 , pp. 248-266
- Sedlak, D.¹ Paguio, A.² Bartunek, P.³

48
- 0037172781
- S. Aliau, H. Mattras, E. Richard, J.-C. Bonnafous, J.-L. Borgna, Biochemistry 2002, 41, 7979-7988
- (2002) Biochemistry , vol.41 , pp. 7979-7988
- Aliau, S.¹ Mattras, H.² Richard, E.³ Bonnafous, J.-C.⁴ Borgna, J.-L.⁵

49
- 78650922889
- X.-M. Fu, P. Wang, B. T. Zhu, Biochemistry 2011, 50, 106-115.
- (2011) Biochemistry , vol.50 , pp. 106-115
- Fu, X.-M.¹ Wang, P.² Zhu, B.T.³

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