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Abstract:

A-homopregnanes and 5β-methylpregnanes were prepared from the easily available 3β-hydroxy-20β-acetoxy-4β,5β-methylenepregnane by cationic and radical rearrangements respectively. The A-homopregnane was formed in a single step upon spontaneous rearrangement and elimination by treatment of the cyclopropyl alcohol with BF3·Et2O. The 5β-methylpregnane was obtained by cleavage of the hydrazone of the corresponding cyclopropylketone followed by rearrangement mediated by mercury(II) hydrides. ©ARKAT.

Registro:

Documento: Artículo
Título:Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes
Autor:Di Chenna, P.H.; Dansey, V.; Ghini, A.A.; Burton, G.
Filiación:Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas Y Naturales, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
Palabras clave:5β-methylpregnane; A-homopregnane; Cyclopropylcarbinyl cation; Cyclopropylcarbinyl radical
Año:2005
Volumen:2005
Número:12
Página de inicio:154
Página de fin:162
Título revista:Arkivoc
Título revista abreviado:Arkivoc
ISSN:14246376
PDF:https://bibliotecadigital.exactas.uba.ar/download/paper/paper_14246376_v2005_n12_p154_DiChenna.pdf
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p154_DiChenna

Referencias:

  • Kantorowsky, E.J., Kurth, M.J., (2000) Tetrahedron, 56, p. 4317
  • Auclair, K., Hu, Z., Little, D.M., Ortiz De Montellano, P.R., Groves, J.T., (2002) J. Am. Chem. Soc., 124, p. 6020
  • Fevill, D.N., Abduljaber, M.H., (2000) J. Org. Chem., 65, p. 2548
  • Haudouin, C., Taran, F., Doris, E., (2001) J. Org. Chem., 66, p. 4450
  • Di Chenna, P.H., Ferrara, A., Ghini, A.A., Burton, G., (2002) J. Chem. Soc., Perkin Trans 1, p. 227
  • Ferrara, A., Burton, G., (1996) Tetrahedron, 37, p. 929
  • Mori, M., Tamaoki, B., (1977) Steroids, 29, p. 517
  • Dauben, W.G., Laug, P., Berezin, G.H., (1966) J. Org. Chem., 31, p. 3869
  • Han, M., Zorumski, C.F., Covey, D.F., (1996) J. Med. Chem., 39, p. 4218

Citas:

---------- APA ----------
Di Chenna, P.H., Dansey, V., Ghini, A.A. & Burton, G. (2005) . Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes. Arkivoc, 2005(12), 154-162.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p154_DiChenna [ ]
---------- CHICAGO ----------
Di Chenna, P.H., Dansey, V., Ghini, A.A., Burton, G. "Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes" . Arkivoc 2005, no. 12 (2005) : 154-162.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p154_DiChenna [ ]
---------- MLA ----------
Di Chenna, P.H., Dansey, V., Ghini, A.A., Burton, G. "Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes" . Arkivoc, vol. 2005, no. 12, 2005, pp. 154-162.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p154_DiChenna [ ]
---------- VANCOUVER ----------
Di Chenna, P.H., Dansey, V., Ghini, A.A., Burton, G. Rearrangement of 4β,5β-methylenepregnanes: A simple approach to A-homopregnanes and 5β-methylpregnanes. Arkivoc. 2005;2005(12):154-162.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p154_DiChenna [ ]