Total Synthesis of the Akuammiline Alkaloid Picrinine

[Image: see text] We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product’...

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Autores principales: Smith, Joel M., Moreno, Jesus, Boal, Ben W., Garg, Neil K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985766/
https://www.ncbi.nlm.nih.gov/pubmed/24597784
http://dx.doi.org/10.1021/ja501780w
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author Smith, Joel M.
Moreno, Jesus
Boal, Ben W.
Garg, Neil K.
author_facet Smith, Joel M.
Moreno, Jesus
Boal, Ben W.
Garg, Neil K.
author_sort Smith, Joel M.
collection PubMed
description [Image: see text] We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product’s carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine.
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spelling pubmed-39857662015-03-05 Total Synthesis of the Akuammiline Alkaloid Picrinine Smith, Joel M. Moreno, Jesus Boal, Ben W. Garg, Neil K. J Am Chem Soc [Image: see text] We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product’s carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine. American Chemical Society 2014-03-05 2014-03-26 /pmc/articles/PMC3985766/ /pubmed/24597784 http://dx.doi.org/10.1021/ja501780w Text en Copyright © 2014 American Chemical Society
spellingShingle Smith, Joel M.
Moreno, Jesus
Boal, Ben W.
Garg, Neil K.
Total Synthesis of the Akuammiline Alkaloid Picrinine
title Total Synthesis of the Akuammiline Alkaloid Picrinine
title_full Total Synthesis of the Akuammiline Alkaloid Picrinine
title_fullStr Total Synthesis of the Akuammiline Alkaloid Picrinine
title_full_unstemmed Total Synthesis of the Akuammiline Alkaloid Picrinine
title_short Total Synthesis of the Akuammiline Alkaloid Picrinine
title_sort total synthesis of the akuammiline alkaloid picrinine
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985766/
https://www.ncbi.nlm.nih.gov/pubmed/24597784
http://dx.doi.org/10.1021/ja501780w
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