6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone

6,19-Methanoprogesterone (4) was synthesized in nine steps from the readily available 3β,20β-diacetyloxy-5α-bromo-6,19,-oxidopregnane (5) in 14% overall yield. The additional carbon atom was introduced by reaction of a C-19 aldehyde with Ph3PCHOCH3 under salt free conditions and subsequent hydrolysi...

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Detalles Bibliográficos
Autores principales: Joselevich, M., Ghini, A.A., Burton, G.
Formato: JOUR
Materias:
Addition reactions
Aldehydes
Atoms
Calculations
Carbon
Conformations
Derivatives
Hydrolysis
Molecular structure
Synthesis (chemical)
Diacetyloxybromooxidopregnane
Lewis acid
Methanoprogesterone
Organic compounds
6,19 methanoprogesterone
6,19-methanoprogesterone
drug derivative
progesterone
steroid
article
chemical model
chemical structure
synthesis
Models, Chemical
Molecular Structure
Progesterone
Steroids
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_14770520_v1_n6_p939_Joselevich
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario:6,19-Methanoprogesterone (4) was synthesized in nine steps from the readily available 3β,20β-diacetyloxy-5α-bromo-6,19,-oxidopregnane (5) in 14% overall yield. The additional carbon atom was introduced by reaction of a C-19 aldehyde with Ph3PCHOCH3 under salt free conditions and subsequent hydrolysis to give the homologous aldehyde. Intramolecular addition of the newly incorporated carbonyl (C-19a) to the olefinic C-6 in ring B was achieved by means of a Prins reaction with TiCl4 as Lewis acid.

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