An aza-Robinson Annulation Strategy for the Synthesis of Fused Bicyclic Amides: Synthesis of (±)-Coniceine and Quinolizidine

[Image: see text] An aza-Robinson annulation strategy is described using a NaOEt-catalyzed conjugate addition of cyclic imides onto vinyl ketones, followed by a TfOH-mediated intramolecular aldol condensation to afford densely functionalized fused bicyclic amides. The potential use of these amides i...

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Autores principales: Garay-Talero, Alexander, Goulart, Tales A. C., Gallo, Rafael D. C., Pinheiro, Roberto do C., Hoyos-Orozco, Catalina, Jurberg, Igor D., Gamba-Sánchez, Diego
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10630962/
https://www.ncbi.nlm.nih.gov/pubmed/37877616
http://dx.doi.org/10.1021/acs.orglett.3c02798
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author Garay-Talero, Alexander
Goulart, Tales A. C.
Gallo, Rafael D. C.
Pinheiro, Roberto do C.
Hoyos-Orozco, Catalina
Jurberg, Igor D.
Gamba-Sánchez, Diego
author_facet Garay-Talero, Alexander
Goulart, Tales A. C.
Gallo, Rafael D. C.
Pinheiro, Roberto do C.
Hoyos-Orozco, Catalina
Jurberg, Igor D.
Gamba-Sánchez, Diego
author_sort Garay-Talero, Alexander
collection PubMed
description [Image: see text] An aza-Robinson annulation strategy is described using a NaOEt-catalyzed conjugate addition of cyclic imides onto vinyl ketones, followed by a TfOH-mediated intramolecular aldol condensation to afford densely functionalized fused bicyclic amides. The potential use of these amides in the synthesis of alkaloids is demonstrated by the sequential conversion of appropriate precursors to (±)-coniceine and quinolizidine in two additional steps, thus allowing their preparation in overall 40 and 44% yields, respectively.
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spelling pubmed-106309622023-11-15 An aza-Robinson Annulation Strategy for the Synthesis of Fused Bicyclic Amides: Synthesis of (±)-Coniceine and Quinolizidine Garay-Talero, Alexander Goulart, Tales A. C. Gallo, Rafael D. C. Pinheiro, Roberto do C. Hoyos-Orozco, Catalina Jurberg, Igor D. Gamba-Sánchez, Diego Org Lett [Image: see text] An aza-Robinson annulation strategy is described using a NaOEt-catalyzed conjugate addition of cyclic imides onto vinyl ketones, followed by a TfOH-mediated intramolecular aldol condensation to afford densely functionalized fused bicyclic amides. The potential use of these amides in the synthesis of alkaloids is demonstrated by the sequential conversion of appropriate precursors to (±)-coniceine and quinolizidine in two additional steps, thus allowing their preparation in overall 40 and 44% yields, respectively. American Chemical Society 2023-10-25 /pmc/articles/PMC10630962/ /pubmed/37877616 http://dx.doi.org/10.1021/acs.orglett.3c02798 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Garay-Talero, Alexander
Goulart, Tales A. C.
Gallo, Rafael D. C.
Pinheiro, Roberto do C.
Hoyos-Orozco, Catalina
Jurberg, Igor D.
Gamba-Sánchez, Diego
An aza-Robinson Annulation Strategy for the Synthesis of Fused Bicyclic Amides: Synthesis of (±)-Coniceine and Quinolizidine
title An aza-Robinson Annulation Strategy for the Synthesis of Fused Bicyclic Amides: Synthesis of (±)-Coniceine and Quinolizidine
title_full An aza-Robinson Annulation Strategy for the Synthesis of Fused Bicyclic Amides: Synthesis of (±)-Coniceine and Quinolizidine
title_fullStr An aza-Robinson Annulation Strategy for the Synthesis of Fused Bicyclic Amides: Synthesis of (±)-Coniceine and Quinolizidine
title_full_unstemmed An aza-Robinson Annulation Strategy for the Synthesis of Fused Bicyclic Amides: Synthesis of (±)-Coniceine and Quinolizidine
title_short An aza-Robinson Annulation Strategy for the Synthesis of Fused Bicyclic Amides: Synthesis of (±)-Coniceine and Quinolizidine
title_sort aza-robinson annulation strategy for the synthesis of fused bicyclic amides: synthesis of (±)-coniceine and quinolizidine
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10630962/
https://www.ncbi.nlm.nih.gov/pubmed/37877616
http://dx.doi.org/10.1021/acs.orglett.3c02798
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