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...

Descripción completa

Guardado en:

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

id	todo:paper_14770520_v1_n6_p939_Joselevich
record_format	dspace
spelling	todo:paper_14770520_v1_n6_p939_Joselevich2023-10-03T16:19:06Z 6,19-carbon-bridged steroids. Synthesis of 6,19-methano-progesterone Joselevich, M. Ghini, A.A. Burton, G. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, M. Ghini, A.A. Burton, G. 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.
format	JOUR
author	Joselevich, M. Ghini, A.A. Burton, G.
author_facet	Joselevich, M. Ghini, A.A. Burton, G.
author_sort	Joselevich, M.
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
url	http://hdl.handle.net/20.500.12110/paper_14770520_v1_n6_p939_Joselevich
work_keys_str_mv	AT joselevichm 619carbonbridgedsteroidssynthesisof619methanoprogesterone AT ghiniaa 619carbonbridgedsteroidssynthesisof619methanoprogesterone AT burtong 619carbonbridgedsteroidssynthesisof619methanoprogesterone
_version_	1807316224975044608

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

Ejemplares similares