Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction

A novel and convenient method utilizing the Aubé reaction to access a new class of compounds that are similar to carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes the Aubé reaction with various cyclic ketones to give cyclopentenyl-substituted lactams. Upon di...

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Autores principales: Shinde, Madhuri V, Ople, Rohini S, Sangtani, Ekta, Gonnade, Rajesh, Reddy, D Srinivasa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4505090/
https://www.ncbi.nlm.nih.gov/pubmed/26199661
http://dx.doi.org/10.3762/bjoc.11.119
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author Shinde, Madhuri V
Ople, Rohini S
Sangtani, Ekta
Gonnade, Rajesh
Reddy, D Srinivasa
author_facet Shinde, Madhuri V
Ople, Rohini S
Sangtani, Ekta
Gonnade, Rajesh
Reddy, D Srinivasa
author_sort Shinde, Madhuri V
collection PubMed
description A novel and convenient method utilizing the Aubé reaction to access a new class of compounds that are similar to carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes the Aubé reaction with various cyclic ketones to give cyclopentenyl-substituted lactams. Upon dihydroxylation, this affords the N-cyclopentenyl-lactam compounds in racemic form. Given the numerous uses of nucleosides and related compounds, we were interested in the synthesis of carbocylic nucleoside mimics. The attempts and results are described herein.
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spelling pubmed-45050902015-07-21 Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction Shinde, Madhuri V Ople, Rohini S Sangtani, Ekta Gonnade, Rajesh Reddy, D Srinivasa Beilstein J Org Chem Full Research Paper A novel and convenient method utilizing the Aubé reaction to access a new class of compounds that are similar to carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes the Aubé reaction with various cyclic ketones to give cyclopentenyl-substituted lactams. Upon dihydroxylation, this affords the N-cyclopentenyl-lactam compounds in racemic form. Given the numerous uses of nucleosides and related compounds, we were interested in the synthesis of carbocylic nucleoside mimics. The attempts and results are described herein. Beilstein-Institut 2015-06-23 /pmc/articles/PMC4505090/ /pubmed/26199661 http://dx.doi.org/10.3762/bjoc.11.119 Text en Copyright © 2015, Shinde 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
Shinde, Madhuri V
Ople, Rohini S
Sangtani, Ekta
Gonnade, Rajesh
Reddy, D Srinivasa
Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction
title Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction
title_full Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction
title_fullStr Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction
title_full_unstemmed Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction
title_short Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction
title_sort synthesis of novel n-cyclopentenyl-lactams using the aubé reaction
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4505090/
https://www.ncbi.nlm.nih.gov/pubmed/26199661
http://dx.doi.org/10.3762/bjoc.11.119
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