E. Sánchez-Fernández, E. Álvarez, C. Ortiz Mellet
Nov 20, 2014
Citations
0
Influential Citations
20
Citations
Journal
The Journal of organic chemistry
Abstract
A practical one-pot synthesis of bi- and triantennated australine analogues from a pivotal sp(2)-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.