Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes

An improved total synthesis of (−)-julocrotine in three steps from Cbz-glutamine, in 51% overall yield, is presented. To demonstrate the potential of the heterocyclic moiety for diversity oriented synthesis, a series of (−)-julocrotine analogues was synthesized by employing the heterocyclic precurso...

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Autores principales: Neves Filho, Ricardo A W, Westermann, Bernhard, Wessjohann, Ludger A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3252850/
https://www.ncbi.nlm.nih.gov/pubmed/22238524
http://dx.doi.org/10.3762/bjoc.7.175
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author Neves Filho, Ricardo A W
Westermann, Bernhard
Wessjohann, Ludger A
author_facet Neves Filho, Ricardo A W
Westermann, Bernhard
Wessjohann, Ludger A
author_sort Neves Filho, Ricardo A W
collection PubMed
description An improved total synthesis of (−)-julocrotine in three steps from Cbz-glutamine, in 51% overall yield, is presented. To demonstrate the potential of the heterocyclic moiety for diversity oriented synthesis, a series of (−)-julocrotine analogues was synthesized by employing the heterocyclic precursor as an amino input in Ugi four-component reactions (Ugi-4CR) [1].
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spelling pubmed-32528502012-01-11 Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes Neves Filho, Ricardo A W Westermann, Bernhard Wessjohann, Ludger A Beilstein J Org Chem Full Research Paper An improved total synthesis of (−)-julocrotine in three steps from Cbz-glutamine, in 51% overall yield, is presented. To demonstrate the potential of the heterocyclic moiety for diversity oriented synthesis, a series of (−)-julocrotine analogues was synthesized by employing the heterocyclic precursor as an amino input in Ugi four-component reactions (Ugi-4CR) [1]. Beilstein-Institut 2011-11-07 /pmc/articles/PMC3252850/ /pubmed/22238524 http://dx.doi.org/10.3762/bjoc.7.175 Text en Copyright © 2011, Neves Filho et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Neves Filho, Ricardo A W
Westermann, Bernhard
Wessjohann, Ludger A
Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes
title Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes
title_full Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes
title_fullStr Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes
title_full_unstemmed Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes
title_short Synthesis of (−)-julocrotine and a diversity oriented Ugi-approach to analogues and probes
title_sort synthesis of (−)-julocrotine and a diversity oriented ugi-approach to analogues and probes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3252850/
https://www.ncbi.nlm.nih.gov/pubmed/22238524
http://dx.doi.org/10.3762/bjoc.7.175
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