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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2016
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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. |
format | Online Article Text |
id | pubmed-4994716 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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