Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry

In this Letter we report that the Ugi reaction/cyclization sequence on a steroidal 17-carboxaldehyde leads to novel steroidal 2,5-diketopiperazines with a noteworthy stereoselectivity. A wide variety in the substitution pattern in the heterocyclic moiety was easily achieved by changing the component...

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Detalles Bibliográficos
Autores principales:	Bruttomesso, Andrea Claudia, Ramirez, Javier Alberto
Publicado:	2009
Materias:	2,5-Diketopiperazines Heterocyclic steroids Multicomponent reaction Ugi reaction 17 carboxaldehyde 2,5 diketopiperazine derivative aldehyde cyanide isocyanide steroid unclassified drug article chemical reaction drug structure drug synthesis stereochemistry ugi reaction
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v50_n28_p4022_Bruttomesso http://hdl.handle.net/20.500.12110/paper_00404039_v50_n28_p4022_Bruttomesso
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00404039_v50_n28_p4022_Bruttomesso
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spelling	paper:paper_00404039_v50_n28_p4022_Bruttomesso2023-06-08T15:04:28Z Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry Bruttomesso, Andrea Claudia Ramirez, Javier Alberto 2,5-Diketopiperazines Heterocyclic steroids Multicomponent reaction Ugi reaction 17 carboxaldehyde 2,5 diketopiperazine derivative aldehyde cyanide isocyanide steroid unclassified drug article chemical reaction drug structure drug synthesis stereochemistry ugi reaction In this Letter we report that the Ugi reaction/cyclization sequence on a steroidal 17-carboxaldehyde leads to novel steroidal 2,5-diketopiperazines with a noteworthy stereoselectivity. A wide variety in the substitution pattern in the heterocyclic moiety was easily achieved by changing the components in the Ugi reaction. © 2009 Elsevier Ltd. All rights reserved. Fil:Bruttomesso, A.C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2009 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v50_n28_p4022_Bruttomesso http://hdl.handle.net/20.500.12110/paper_00404039_v50_n28_p4022_Bruttomesso
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	2,5-Diketopiperazines Heterocyclic steroids Multicomponent reaction Ugi reaction 17 carboxaldehyde 2,5 diketopiperazine derivative aldehyde cyanide isocyanide steroid unclassified drug article chemical reaction drug structure drug synthesis stereochemistry ugi reaction
spellingShingle	2,5-Diketopiperazines Heterocyclic steroids Multicomponent reaction Ugi reaction 17 carboxaldehyde 2,5 diketopiperazine derivative aldehyde cyanide isocyanide steroid unclassified drug article chemical reaction drug structure drug synthesis stereochemistry ugi reaction Bruttomesso, Andrea Claudia Ramirez, Javier Alberto Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry
topic_facet	2,5-Diketopiperazines Heterocyclic steroids Multicomponent reaction Ugi reaction 17 carboxaldehyde 2,5 diketopiperazine derivative aldehyde cyanide isocyanide steroid unclassified drug article chemical reaction drug structure drug synthesis stereochemistry ugi reaction
description	In this Letter we report that the Ugi reaction/cyclization sequence on a steroidal 17-carboxaldehyde leads to novel steroidal 2,5-diketopiperazines with a noteworthy stereoselectivity. A wide variety in the substitution pattern in the heterocyclic moiety was easily achieved by changing the components in the Ugi reaction. © 2009 Elsevier Ltd. All rights reserved.
author	Bruttomesso, Andrea Claudia Ramirez, Javier Alberto
author_facet	Bruttomesso, Andrea Claudia Ramirez, Javier Alberto
author_sort	Bruttomesso, Andrea Claudia
title	Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry
title_short	Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry
title_full	Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry
title_fullStr	Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry
title_full_unstemmed	Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry
title_sort	highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry
publishDate	2009
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v50_n28_p4022_Bruttomesso http://hdl.handle.net/20.500.12110/paper_00404039_v50_n28_p4022_Bruttomesso
work_keys_str_mv	AT bruttomessoandreaclaudia highlystereoselectivesynthesisofsteroidal25diketopiperazinesbasedonisocyanidechemistry AT ramirezjavieralberto highlystereoselectivesynthesisofsteroidal25diketopiperazinesbasedonisocyanidechemistry
_version_	1768544310857302016

Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry

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