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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Autores principales:	Bruttomesso, A.C., Eiras, J., Ramírez, J.A., Galagovsky, L.R.
Formato:	JOUR
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:	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	todo:paper_00404039_v50_n28_p4022_Bruttomesso
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spelling	todo:paper_00404039_v50_n28_p4022_Bruttomesso2023-10-03T14:50:56Z Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry Bruttomesso, A.C. Eiras, J. Ramírez, J.A. Galagovsky, L.R. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, A.C. Eiras, J. Ramírez, J.A. Galagovsky, L.R. 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.
format	JOUR
author	Bruttomesso, A.C. Eiras, J. Ramírez, J.A. Galagovsky, L.R.
author_facet	Bruttomesso, A.C. Eiras, J. Ramírez, J.A. Galagovsky, L.R.
author_sort	Bruttomesso, A.C.
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
url	http://hdl.handle.net/20.500.12110/paper_00404039_v50_n28_p4022_Bruttomesso
work_keys_str_mv	AT bruttomessoac highlystereoselectivesynthesisofsteroidal25diketopiperazinesbasedonisocyanidechemistry AT eirasj highlystereoselectivesynthesisofsteroidal25diketopiperazinesbasedonisocyanidechemistry AT ramirezja highlystereoselectivesynthesisofsteroidal25diketopiperazinesbasedonisocyanidechemistry AT galagovskylr highlystereoselectivesynthesisofsteroidal25diketopiperazinesbasedonisocyanidechemistry
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Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry

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