Stereoselective synthesis of a dioxa-bicyclo[3.2.1]octane SGLT2 inhibitor.
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.
Mascitti
Vincent
V
Pfizer Global Research and Development, Groton, Connecticut 06340, USA. vincent.mascitti@pfizer.com
Préville
Cathy
C
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008968:Molecular Conformation; D000077203:Sodium-Glucose Transporter 2 Inhibitors; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D000077203:Sodium-Glucose Transporter 2 Inhibitors; C493209:dioxabicyclo(3.2.1)octane