Abstract:
The copper-catalyzed reaction of [N-(Ses)imino]phenyliodinane with 11-pregnene-3,20-dione gave the corresponding aziridine in 53% yield. The Ses protecting group could be conveniently removed using the TASF reagent. Furthermore, nucleophilic ring opening of the protected N-Ses-aziridine with thiophenol in the presence of a Lewis acid led to introduction of the thiophenol group at the α-12 position but, unexpectedly, concomitant loss of the Ses group to provide compound 10.© 2000 Elsevier Science Ltd.
Registro:
Documento: |
Artículo
|
Título: | Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses |
Autor: | Di Chenna, P.H.; Dauban, P.; Ghini, A.; Burton, G.; Dodd, R.H. |
Filiación: | Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina Institut de Chimie des Substances Naturelles, C.N.R.S., 91198 Gif-sur-Yvette Cedex, France
|
Palabras clave: | 11 pregnene 3,20 dione; aziridine derivative; pregnane derivative; steroid; unclassified drug; article; chemical reaction; nuclear Overhauser effect; proton nuclear magnetic resonance; reduction; stereochemistry; stereoisomerism; steroidogenesis; synthesis |
Año: | 2000
|
Volumen: | 41
|
Número: | 36
|
Página de inicio: | 7041
|
Página de fin: | 7045
|
DOI: |
http://dx.doi.org/10.1016/S0040-4039(00)01228-4 |
Título revista: | Tetrahedron Letters
|
Título revista abreviado: | Tetrahedron Lett.
|
ISSN: | 00404039
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v41_n36_p7041_DiChenna |
Referencias:
- Njar, V.C.O., Hector, M., Hartmann, R.W., (1996) Bioorg. Med. Chem., 4, p. 1447
- Ling, Y., Li, J., Kato, K., Liu, Y., Wang, X., Klus, G.T., Marat, K., Brodie, A.M.H., (1998) Bioorg. Med. Chem., 6, p. 1683
- Njar, V.C.O., Hartmann, R.W., Robinson, C.H., (1995) J. Chem. Soc., Perkin Trans. 1, p. 985
- Njar, V.C.O., Safi, E., Silverton, J.V., Robinson, C.H., (1993) J. Chem. Soc., Perkin Trans. 1, p. 1161
- Aliau, S., Mattras, H., Richard, E., Borgna, J.-L., (1999) Biochemistry, 38, p. 14752
- Hope, C.E., (1981) Can. Anaesth. Soc. J., 28, p. 1
- Marshall, F.H., Stratton, S.C., Mullings, J., Ford, E., Worton, S.P., Oakley, N.R., Hagan, R.M., (1997) Pharmacol. Biochem. Behav., 58, p. 1
- Anderson, A., Boyd, A.C., Byford, A., Campbell, A.C., Gemmell, D.K., Hamilton, N.M., Hill, D.R., Sundaram, H., (1997) J. Med. Chem., 40, p. 1668
- Gasior, M., Carter, R.B., Witkin, J.M., (1999) Trends Pharmacol. Sci., 20, p. 107
- Beuchet, P., El Kihel, L., Dherbomez, M., Charles, G., Letourneux, Y., (1998) Bioorg. Med. Chem. Lett., 8, p. 3627
- Fioravanti, S., Pellacani, L., Tabanella, S., Tardella, P.A., (1998) Tetrahedron, 54, p. 14105
- Evans, D.A., Faul, M.M., Bilodeau, M.T., (1994) J. Am. Chem. Soc., 116, p. 2742
- Muller, P., (1996), 2, pp. 113-151. , For a review on transition metal-catalyzed nitrene transfer reactions, Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, CT; Sodergren, M.J., Alonso, D.A., Bedekar, A.V., Andersson, P.G., (1997) Tetrahedron Lett., 38, p. 6897
- Dauban, P., Dodd, R.H., (1998) Tetrahedron Lett., 39, p. 5739
- Dauban, P., Dodd, R.H., (2000) Org. Lett., 2, p. 2327
- Dauban, P., Dodd, R.H., (1999) J. Org. Chem., 64, p. 5304
- Lambert, J.J., Belelli, D., Hill-Venning, C., Peters, J.A., (1995) Trends Pharmacol. Sci., 16, p. 295
- Scheidt, K.A., Chen, H., Follows, B.C., Chemler, S.R., Coffey, D.S., Roush, W.R., (1998) J. Org. Chem., 63, p. 6436
- Legters, J., Thijs, L., Zwanenburg, B., (1992) Recl. Trav. Chim. Pays-Bas, 111, p. 16
- Takeuchi, H., Koyama, K., (1981) J. Chem. Soc., Perkin Trans 2, p. 121
- Lin, P.-Y., Bellos, K., Stamm, H., Onistschenko, A., (1992) Tetrahedron, 48, p. 2359
- Yang, J., Weinberg, R., Breslow, R., (2000) Chem. Commun., p. 531
- Broess, A.I.A., Van Vliet, N.P., Groen, M.B., Hamersma, H., (1992) Steroids, 57, p. 514
Citas:
---------- APA ----------
Di Chenna, P.H., Dauban, P., Ghini, A., Burton, G. & Dodd, R.H.
(2000)
. Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses. Tetrahedron Letters, 41(36), 7041-7045.
http://dx.doi.org/10.1016/S0040-4039(00)01228-4---------- CHICAGO ----------
Di Chenna, P.H., Dauban, P., Ghini, A., Burton, G., Dodd, R.H.
"Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses"
. Tetrahedron Letters 41, no. 36
(2000) : 7041-7045.
http://dx.doi.org/10.1016/S0040-4039(00)01228-4---------- MLA ----------
Di Chenna, P.H., Dauban, P., Ghini, A., Burton, G., Dodd, R.H.
"Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses"
. Tetrahedron Letters, vol. 41, no. 36, 2000, pp. 7041-7045.
http://dx.doi.org/10.1016/S0040-4039(00)01228-4---------- VANCOUVER ----------
Di Chenna, P.H., Dauban, P., Ghini, A., Burton, G., Dodd, R.H. Aziridination of 11-pregnene-3,20-dione using PhI=N-Ses. Tetrahedron Lett. 2000;41(36):7041-7045.
http://dx.doi.org/10.1016/S0040-4039(00)01228-4