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Volumn 5, Issue 1, 2008, Pages 17-21

Steroidal δ-alkenyl oximes as ambident nucleophiles: Electrophile-induced formation of oxazepane derivatives in the bis-estrone series

Author keywords

1,3 dipolar cycloadditions; Dimeric steroids; Estrone derivatives; Oxazepane; Selenium; Stereoselectivity

Indexed keywords

EID: 38949196459 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017808783330243 Document Type: Article

Times cited : (11)

References (27)

1
- 0036136604
- (a) Dondas, H.A.; Grigg, R.; Markandu, J.; Perrior, T.; Suzuki, T.; Thibault, S.; Thomas W.A.; Thornton-Pett, M. Tetrahedron, 2002, 58, 161.
- (2002) Tetrahedron , vol.58 , pp. 161
- Dondas, H.A.¹ Grigg, R.² Markandu, J.³ Perrior, T.⁴ Suzuki, T.⁵ Thibault, S.⁶ Thomas, W.A.⁷ Thornton-Pett, M.⁸

2
- 0034670538
- (b) Dondas, H.A.; Grigg, R.; Hadjisoteriou, M.; Markandu, J.; Thomas W.A.; Kennewell, P. Tetrahedron, 2000, 56, 10087.
- (2000) Tetrahedron , vol.56 , pp. 10087
- Dondas, H.A.¹ Grigg, R.² Hadjisoteriou, M.³ Markandu, J.⁴ Thomas, W.A.⁵ Kennewell, P.⁶

3
- 0001106752
- (c) Dondas, H.A.; Grigg, R.; Frampton, S. Tetrahedon Lett., 1997, 38, 5719.
- (1997) Tetrahedon Lett , vol.38 , pp. 5719
- Dondas, H.A.¹ Grigg, R.² Frampton, S.³

4
- 30744440089
- (a) Tiecco, M.; Testaferri L.; Bagnoli, L.; Marini, F.; Santi, C.; Temperini, A.; Scarponi, C.; Sternativo, S.; Terlizzi, R.; Tomassini, C. Arkivoc, 2006, 7, 186.
- (2006) Arkivoc , vol.7 , pp. 186
- Tiecco, M.¹ Testaferri, L.² Bagnoli, L.³ Marini, F.⁴ Santi, C.⁵ Temperini, A.⁶ Scarponi, C.⁷ Sternativo, S.⁸ Terlizzi, R.⁹ Tomassini, C.¹⁰

5
- 0035931036
- (b) Tiecco, M.; Testaferri L.; Bagnoli, L.; Purgatorio, V.; Temperini, A.; Marini, F.; Santi, C. Tetrahedron Asymmetry, 2001, 12, 3297.
- (2001) Tetrahedron Asymmetry , vol.12 , pp. 3297
- Tiecco, M.¹ Testaferri, L.² Bagnoli, L.³ Purgatorio, V.⁴ Temperini, A.⁵ Marini, F.⁶ Santi, C.⁷

6
- 15444363542
- Mernyák, E.; Benedek, G.; Schneider, G.; Wölfling, J. Synlett., 2005, 637.
- (2005) Synlett , pp. 637
- Mernyák, E.¹ Benedek, G.² Schneider, G.³ Wölfling, J.⁴

7
- 0037100292
- Dondas, H.A.; Grigg, R.; Thibault, S.; Thomas W.A.; Thornton-Pett, M. Tetrahedron, 2002, 58, 5827.
- (2002) Tetrahedron , vol.58 , pp. 5827
- Dondas, H.A.¹ Grigg, R.² Thibault, S.³ Thomas, W.A.⁴ Thornton-Pett, M.⁵

8
- 0018671747
- (a) Banks, C.H.; Daniel, J.R.; Zingaro, R.A. J. Med. Chem., 1979, 22, 572.
- (1979) J. Med. Chem , vol.22 , pp. 572
- Banks, C.H.¹ Daniel, J.R.² Zingaro, R.A.³

9
- 38949090992
- U.S. Patent, 3,952,030
- (b) Chambers, V.E.M.; Riley, A.L.M. U.S. Patent, 1976, 3,952,030.
- (1976)
- Chambers, V.E.M.¹ Riley, A.L.M.²

10
- 0020095332
- (c) Longcope, C.; Arunachalam, T.; Caspi, E. Can. J. Biochem., 1982, 60, 152.
- (1982) Can. J. Biochem , vol.60 , pp. 152
- Longcope, C.¹ Arunachalam, T.² Caspi, E.³

11
- 38949105819
- (d) Napolitano, E.; Fiaschi, R.; Herman, L.W.; Hanson, R.N. Steroids, 1996, 61, 394.
- (1996) Steroids , vol.61 , pp. 394
- Napolitano, E.¹ Fiaschi, R.² Herman, L.W.³ Hanson, R.N.⁴

12
- 0019487172
- (e) Arunachalam, T.; Caspi, E. J. Org. Chem., 1981, 46, 3415.
- (1981) J. Org. Chem , vol.46 , pp. 3415
- Arunachalam, T.¹ Caspi, E.²

13
- 0019465372
- (f) Sadek, S.A.; Shaw, S.M. Kessler, W.V.; Wolf, G.C. J. Org. Chem., 1981, 46, 3259.
- (1981) J. Org. Chem , vol.46 , pp. 3259
- Sadek, S.A.¹ Shaw, S.M.² Kessler, W.V.³ Wolf, G.C.⁴

14
- 0020365043
- (g) Sadek, S.A.; Kessler, W.V.; Shaw, S.M.; Anderson, J.N.; Wolf, G.C. J. Med. Chem., 1982, 25, 1488.
- (1982) J. Med. Chem , vol.25 , pp. 1488
- Sadek, S.A.¹ Kessler, W.V.² Shaw, S.M.³ Anderson, J.N.⁴ Wolf, G.C.⁵

15
- 38949088593
- PhSeBr-induced cyclization in the 13β-estrone series: Oxime 1 (1 mmol) or oxime O-benzyl ether 2 (1 mmol) was dissolved in dry MeCN (15 ml) and PhSeBr (1 mmol) was added at room temperature under a N2 atmosphere. The mixture was stirred for 0.5 h. The precipitate was filtered off, washed with cold, dry MeCN and dried in the air. The crude product needed no purification, though it could be purified by flash chromatography, with elution with CH2Cl2, to give the product 14b as white crystals. Data for 14b: Mp 204-206 °C; 1H NMR (600 MHz, CDCl3, δ0.97 (s, 3H, 18-H3, 1.08 (s, 3H, 18′-H3, 2.78-2.90 (overlapping multiplets, 5H, 6-H2, 6′-H2, 16-H, 2.96 (dd, 1H, J, 12.2 Hz, J, 9.6 Hz) and 3.30 (dd, 1H, J, 12.2 Hz, J, 1.5 Hz, 16a′-H2, 3.09 dd, 1H, J, 12.3 Hz, J, 8.2 H
- 2; C, 66.66; H, 6.67; N, 2.99. Found: C, 66.92; H, 6.50; N, 3.08.

16
- 84982443772
- (a) Padwa, A. Angew. Chem. Int. Ed., 1976, 15, 123.
- (1976) Angew. Chem. Int. Ed , vol.15 , pp. 123
- Padwa, A.¹

17
- 33947231700
- (b) Pellissier, H. Tetrahedron, 2007, 63, 3235.
- (2007) Tetrahedron , vol.63 , pp. 3235
- Pellissier, H.¹

18
- 38949201619
- MOPAC2007, James J. P. Stewart, Stewart Computational Chemistry, Version 7.101
- MOPAC2007, James J. P. Stewart, Stewart Computational Chemistry, Version 7.101.

19
- 38949173139
- PhSeBr-induced cyclization in the 13α-estrone series: Oxime 15 (1 mmol) or oxime O-benzyl ether 16 (1 mmol) was dissolved in dry MeCN (15 ml) and PhSeBr (1 mmol) was added at room temperature under a N2 atmosphere. The mixture was stirred for 24 h. The solvent was evaporated off, the crude product was dissolved in CH2Cl2 (5 ml, and MeOH (5 ml) was added, and reduction was carried out with KBH4 (2 mmol) during 3 h under stirring. The reaction mixture was transferred to a separatory funnel, CH2Cl2 (2C ml) was added, and the organic phase was washed with water. The CH2Cl2 solution was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The resulting oil was subjected to flash chromatography with CH2Cl2 in the case of oxime 15, and with gradient elution starting with 70% CH2Cl2/30% hexane
- 33NOSe; C, 68.71; H, 7.32; N, 3.08. Found: C, 68.54; H, 7.48; N, 2.90.

20
- 0038694963
- Schönecker, B.; Lange, C.; Kötteritzsch, M.; Günther, W.; Weston, J.; Anders, E.; Görls, H. J. Org. Chem., 2000, 65, 5487.
- (2000) J. Org. Chem , vol.65 , pp. 5487
- Schönecker, B.¹ Lange, C.² Kötteritzsch, M.³ Günther, W.⁴ Weston, J.⁵ Anders, E.⁶ Görls, H.⁷

21
- 0028127325
- (a) Grinsteiner, T.; Kishi, Y. Tetrahedron Lett., 1994, 3 5, 8337.
- (1994) Tetrahedron Lett , vol.3 , Issue.5 , pp. 8337
- Grinsteiner, T.¹ Kishi, Y.²

22
- 3142757947
- (b) Knöpfel, T.F.; Boyall, D.; Carreira, E.M. Org. Lett., 2004, 6, 2281.
- (2004) Org. Lett , vol.6 , pp. 2281
- Knöpfel, T.F.¹ Boyall, D.² Carreira, E.M.³

23
- 0034693109
- (c) Räcker, R.; Döring, K.; Reiser, O. J. Org. Chem., 2000, 65, 6932.
- (2000) J. Org. Chem , vol.65 , pp. 6932
- Räcker, R.¹ Döring, K.² Reiser, O.³

24
- 0032532258
- (d) Hoberg, J.O. Tetrahedron, 1998, 54, 12631.
- (1998) Tetrahedron , vol.54 , pp. 12631
- Hoberg, J.O.¹

25
- 0000097162
- (a) Li, Y.X.; Dias, J.R. Chem. Rev., 1997, 97, 283.
- (1997) Chem. Rev , vol.97 , pp. 283
- Li, Y.X.¹ Dias, J.R.²

26
- 0000591172
- (b) Guthrie, J.P.; Cossar, J.; Darson, B.A. Can. J. Chem., 1986, 64, 2456.
- (1986) Can. J. Chem , vol.64 , pp. 2456
- Guthrie, J.P.¹ Cossar, J.² Darson, B.A.³

27
- 34248545237
- (c) Nahar, L.; Sarker, S.D.; Turner, A.B. Curr. Med. Chem., 2007, 14, 1349.
- (2007) Curr. Med. Chem , vol.14 , pp. 1349
- Nahar, L.¹ Sarker, S.D.² Turner, A.B.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.