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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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Detalles Bibliográficos
Autores principales: Lin, Jing, Qiu, Xiao-Long, Qing, Feng-Ling
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
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
Descripción
Sumario: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.