Synthesis of branched iminosugars through a hypervalent iodine(III)-mediated radical-polar crossover reaction
- Santana, Andrés G.
- Paz, Nieves R.
- Francisco, Cosme G.
- Suárez, Ernesto
- González Martín, Concepción C.
DOIAbstract
The 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.T...
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