Pintu Das, S. Ajay, A. Shaw
Jun 29, 2016
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Influential Citations
7
Citations
Journal
Synthesis
Abstract
Abstract The synthesis of d-fagomine and its seven- and eight-membered higher-ring analogues from commercially available l-xylose is reported. The syntheses involve elaboration of a common alkenol precursor obtained from l-xylose-derived hemiacetal. The key steps in the syntheses are intramolecular reductive amination and ring-closing metathesis for the synthesis of d-fagomine and seven-/eight-membered iminosugar, respectively. We have also extended our synthetic strategy for the formal synthesis of (+)-australine using zinc-mediated fragmentation reaction and ring-closing metathesis as key steps.