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Synthesis of branched iminosugars through a hypervalent iodine(III)-mediated radical-polar crossover reaction

AuthorsSantana, Andrés G. ; Paz, Nieves R.; Francisco, Cosme G. ; Suárez, Ernesto ; González Martín, Concepción C.
Issue Date8-Jul-2013
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 78(15): 7527-7543 (2013)
AbstractThe synthesis of a novel type of branched iminosugars is described. This synthetic strategy is based on two key reactions: first, an aldol reaction with formaldehyde in order to introduce selectively the hydroxymethyl branch, and second, a tandem β-fragmentation-intramolecular cyclization reaction. The combination of both reactions afforded a battery of compounds exhibiting a great structural complexity, with the concomitant formation of a quaternary center, starting from readily available aldoses. With this approach we have demonstrated the usefulness of the fragmentation of anomeric alkoxyl radicals (ARF) promoted by the PhIO/I2 system for the preparation of new compounds with potential interest for both medicinal and synthetic chemists.
Publisher version (URL)https://pubs.acs.org/doi/ipdf/10.1021/jo401041s
Identifiersdoi: 10.1021/jo401041s
issn: 0022-3263
e-issn: 1520-6904
Appears in Collections:(IPNA) Artículos
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