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Stereoselective Synthesis of a Dioxa-bicyclo[3.2.1]octane SGLT2 Inhibitor

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journal contribution
posted on 02.07.2010, 00:00 by Vincent Mascitti, Cathy Préville
A promising class of SGLT2 inhibitors bearing a unique dioxa-bicyclo[3.2.1]octane motif was recently disclosed. An improved stereoselective synthesis providing efficient access to one of the most potent and selective compounds from this class is reported. A one-pot deprotection/cyclization was used as the key step to form the dioxa-bicyclo[3.2.1]octane motif with full control of stereochemistry. Using an appropriately substituted aryl group, the route enables the synthesis of any given compound from the class.