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Abstract:

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.

Registro:

Documento: Artículo
Título:Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry
Autor:Bruttomesso, A.C.; Eiras, J.; Ramírez, J.A.; Galagovsky, L.R.
Filiación:Departamento de Quimica Organica and UMYMFOR (CONICET-Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellon 2, Piso 3, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
Palabras clave: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
Año:2009
Volumen:50
Número:28
Página de inicio:4022
Página de fin:4024
DOI: http://dx.doi.org/10.1016/j.tetlet.2009.03.219
Título revista:Tetrahedron Letters
Título revista abreviado:Tetrahedron Lett.
ISSN:00404039
CODEN:TELEA
CAS:cyanide, 57-12-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v50_n28_p4022_Bruttomesso

Referencias:

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Citas:

---------- APA ----------
Bruttomesso, A.C., Eiras, J., Ramírez, J.A. & Galagovsky, L.R. (2009) . Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry. Tetrahedron Letters, 50(28), 4022-4024.
http://dx.doi.org/10.1016/j.tetlet.2009.03.219
---------- CHICAGO ----------
Bruttomesso, A.C., Eiras, J., Ramírez, J.A., Galagovsky, L.R. "Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry" . Tetrahedron Letters 50, no. 28 (2009) : 4022-4024.
http://dx.doi.org/10.1016/j.tetlet.2009.03.219
---------- MLA ----------
Bruttomesso, A.C., Eiras, J., Ramírez, J.A., Galagovsky, L.R. "Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry" . Tetrahedron Letters, vol. 50, no. 28, 2009, pp. 4022-4024.
http://dx.doi.org/10.1016/j.tetlet.2009.03.219
---------- VANCOUVER ----------
Bruttomesso, A.C., Eiras, J., Ramírez, J.A., Galagovsky, L.R. Highly stereoselective synthesis of steroidal 2,5-diketopiperazines based on isocyanide chemistry. Tetrahedron Lett. 2009;50(28):4022-4024.
http://dx.doi.org/10.1016/j.tetlet.2009.03.219