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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Autores principales: Joselevich, María, Ghini, Alberto Antonio, Burton, Gerardo
Publicado: 2003
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:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v1_n6_p939_Joselevich
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
id paper:paper_14770520_v1_n6_p939_Joselevich
record_format dspace
spelling paper:paper_14770520_v1_n6_p939_Joselevich2023-06-08T16:18:05Z 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone Joselevich, María Ghini, Alberto Antonio Burton, Gerardo 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 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. Fil:Joselevich, M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ghini, A.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2003 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v1_n6_p939_Joselevich http://hdl.handle.net/20.500.12110/paper_14770520_v1_n6_p939_Joselevich
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 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
spellingShingle 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
Joselevich, María
Ghini, Alberto Antonio
Burton, Gerardo
6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone
topic_facet 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
description 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.
author Joselevich, María
Ghini, Alberto Antonio
Burton, Gerardo
author_facet Joselevich, María
Ghini, Alberto Antonio
Burton, Gerardo
author_sort Joselevich, María
title 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone
title_short 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone
title_full 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone
title_fullStr 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone
title_full_unstemmed 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone
title_sort 6,19-carbon-bridged steroids. synthesis of 6,19-methano-progesterone
publishDate 2003
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v1_n6_p939_Joselevich
http://hdl.handle.net/20.500.12110/paper_14770520_v1_n6_p939_Joselevich
work_keys_str_mv AT joselevichmaria 619carbonbridgedsteroidssynthesisof619methanoprogesterone
AT ghinialbertoantonio 619carbonbridgedsteroidssynthesisof619methanoprogesterone
AT burtongerardo 619carbonbridgedsteroidssynthesisof619methanoprogesterone
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