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Expeditious Synthesis of a Common Intermediate of l-1-Deoxyallonojirimycin and l-1-Deoxymannojirimycin

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journal contribution
posted on 06.03.2009, 00:00 by Franck Ferreira, Candice Botuha, Fabrice Chemla, Alejandro Pérez-Luna
The expeditious synthesis of a common intermediate of l-1-deoxyallonojirimycin (l-allo-DNJ) and l-1-deoxymannojirimycin (l-manno-DNJ) is reported. This intermediate is obtained in highly diastereo- and enantioselectivity with 38.4% overall yield in six steps involving the unprecedented ring-closing metathesis of a tert-butylsulfinyl allylamine as the key step.