A Route to the C,D,E Ring System of the Aspidosperma Alkaloids

[Image: see text] A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product...

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Autores principales: Giampa, Geoffrey M., Fang, Jian, Brewer, Matthias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4994716/
https://www.ncbi.nlm.nih.gov/pubmed/27500799
http://dx.doi.org/10.1021/acs.orglett.6b01674
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author Giampa, Geoffrey M.
Fang, Jian
Brewer, Matthias
author_facet Giampa, Geoffrey M.
Fang, Jian
Brewer, Matthias
author_sort Giampa, Geoffrey M.
collection PubMed
description [Image: see text] A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product as a single diastereomer. A γ-amino-β-hydroxy-α-diazo carbonyl compound is shown to fragment in the presence of a Lewis acid to give an iminium product that can be directly reduced to the corresponding amine.
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spelling pubmed-49947162017-08-08 A Route to the C,D,E Ring System of the Aspidosperma Alkaloids Giampa, Geoffrey M. Fang, Jian Brewer, Matthias Org Lett [Image: see text] A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product as a single diastereomer. A γ-amino-β-hydroxy-α-diazo carbonyl compound is shown to fragment in the presence of a Lewis acid to give an iminium product that can be directly reduced to the corresponding amine. American Chemical Society 2016-08-08 2016-08-19 /pmc/articles/PMC4994716/ /pubmed/27500799 http://dx.doi.org/10.1021/acs.orglett.6b01674 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Giampa, Geoffrey M.
Fang, Jian
Brewer, Matthias
A Route to the C,D,E Ring System of the Aspidosperma Alkaloids
title A Route to the C,D,E Ring System of the Aspidosperma Alkaloids
title_full A Route to the C,D,E Ring System of the Aspidosperma Alkaloids
title_fullStr A Route to the C,D,E Ring System of the Aspidosperma Alkaloids
title_full_unstemmed A Route to the C,D,E Ring System of the Aspidosperma Alkaloids
title_short A Route to the C,D,E Ring System of the Aspidosperma Alkaloids
title_sort route to the c,d,e ring system of the aspidosperma alkaloids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4994716/
https://www.ncbi.nlm.nih.gov/pubmed/27500799
http://dx.doi.org/10.1021/acs.orglett.6b01674
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