Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides

The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl p...

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Autores principales: Jaffer, Mileina, Ebead, Abdelaziz, Lee-Ruff, Edward
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264288/
https://www.ncbi.nlm.nih.gov/pubmed/20657410
http://dx.doi.org/10.3390/molecules15063816
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author Jaffer, Mileina
Ebead, Abdelaziz
Lee-Ruff, Edward
author_facet Jaffer, Mileina
Ebead, Abdelaziz
Lee-Ruff, Edward
author_sort Jaffer, Mileina
collection PubMed
description The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation of an isonucleoside uses a cyclobutanone with an α-substituted 6-chloropurine. Irradiation of the latter produces an isonucleoside and acyclic nucleoside analogues.
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spelling pubmed-62642882018-12-04 Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides Jaffer, Mileina Ebead, Abdelaziz Lee-Ruff, Edward Molecules Article The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation of an isonucleoside uses a cyclobutanone with an α-substituted 6-chloropurine. Irradiation of the latter produces an isonucleoside and acyclic nucleoside analogues. MDPI 2010-05-26 /pmc/articles/PMC6264288/ /pubmed/20657410 http://dx.doi.org/10.3390/molecules15063816 Text en © 2010 by the authors; licensee MDPI, Basel, Switzerland. This article is an Open Access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Jaffer, Mileina
Ebead, Abdelaziz
Lee-Ruff, Edward
Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
title Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
title_full Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
title_fullStr Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
title_full_unstemmed Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
title_short Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
title_sort photochemical synthesis of nucleoside analogues from cyclobutanones: bicyclic and isonucleosides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264288/
https://www.ncbi.nlm.nih.gov/pubmed/20657410
http://dx.doi.org/10.3390/molecules15063816
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