Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone

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3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue...

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Detalles Bibliográficos
Autores principales: Eduardo, S.L., Ghini, A.A., Burton, G.
Formato: JOUR
Materias:
2,19-Oxido-allopregnanolone
4,19-oxido-allopregnanolone
Neurosteroid
Oxido-bridged steroid
19 hydroxy 2alpha,3alpha epoxypregnane
19 hydroxypregnenolone 3 acetate
3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one
3alpha hydroxy 5alphah pregnan 20 one
4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one
bridged compound
neurosteroid
silane derivative
unclassified drug
article
cyclization
desilylation
drug structure
drug synthesis
structure activity relation
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p468_Eduardo
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario:3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue was obtained as a byproduct upon cyclization of the isomeric 3α,4α-epoxide.

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