Synthesis of gem-difluoromethylenated analogues of boronolide

The straightforward synthesis of four gem-difluoromethylenated analogues 4–7 of boronolide is described. The key steps of the synthesis include the concise preparation of the key intermediates 12a–b through the indium-mediated gem-difluoropropargylation of aldehyde 9 with the fluorine-containing bui...

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Autores principales: Lin, Jing, Qiu, Xiao-Long, Qing, Feng-Ling
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874314/
https://www.ncbi.nlm.nih.gov/pubmed/20502653
http://dx.doi.org/10.3762/bjoc.6.37
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author Lin, Jing
Qiu, Xiao-Long
Qing, Feng-Ling
author_facet Lin, Jing
Qiu, Xiao-Long
Qing, Feng-Ling
author_sort Lin, Jing
collection PubMed
description The straightforward synthesis of four gem-difluoromethylenated analogues 4–7 of boronolide is described. The key steps of the synthesis include the concise preparation of the key intermediates 12a–b through the indium-mediated gem-difluoropropargylation of aldehyde 9 with the fluorine-containing building block 11 and the efficient construction of α,β-unsaturated-δ-lactones 15a–b via BAIB/TEMPO-procedure.
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spelling pubmed-28743142010-05-25 Synthesis of gem-difluoromethylenated analogues of boronolide Lin, Jing Qiu, Xiao-Long Qing, Feng-Ling Beilstein J Org Chem Full Research Paper The straightforward synthesis of four gem-difluoromethylenated analogues 4–7 of boronolide is described. The key steps of the synthesis include the concise preparation of the key intermediates 12a–b through the indium-mediated gem-difluoropropargylation of aldehyde 9 with the fluorine-containing building block 11 and the efficient construction of α,β-unsaturated-δ-lactones 15a–b via BAIB/TEMPO-procedure. Beilstein-Institut 2010-04-20 /pmc/articles/PMC2874314/ /pubmed/20502653 http://dx.doi.org/10.3762/bjoc.6.37 Text en Copyright © 2010, Lin et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Lin, Jing
Qiu, Xiao-Long
Qing, Feng-Ling
Synthesis of gem-difluoromethylenated analogues of boronolide
title Synthesis of gem-difluoromethylenated analogues of boronolide
title_full Synthesis of gem-difluoromethylenated analogues of boronolide
title_fullStr Synthesis of gem-difluoromethylenated analogues of boronolide
title_full_unstemmed Synthesis of gem-difluoromethylenated analogues of boronolide
title_short Synthesis of gem-difluoromethylenated analogues of boronolide
title_sort synthesis of gem-difluoromethylenated analogues of boronolide
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874314/
https://www.ncbi.nlm.nih.gov/pubmed/20502653
http://dx.doi.org/10.3762/bjoc.6.37
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