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Synthesis of Multibranched Australine Derivatives from Reducing Castanospermine Analogues through the Amadori Rearrangement of gem-Diamine Intermediates: Selective Inhibitors of β‑Glucosidase

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journal contribution
posted on 05.12.2014, 00:00 by Elena M. Sánchez-Fernández, Eleuterio Álvarez, Carmen Ortiz Mellet, José M. García Fernández
A practical one-pot synthesis of bi- and triantennated australine analogues from a pivotal sp2-iminosugar-type reducing castanospermine precursor is reported. The transformation involves a gem-diamine intermediate that undergoes the indolizidine → pyrrolizidine Amadori-type rearrangement and proceeds under strict control of the generalized anomeric effect to afford a single diastereomer. The final compounds behave as selective competitive inhibitors of β-glucosidase and are promising candidates as pharmacological chaperones for Gaucher disease.

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