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.

近期，一类具有独特二氧杂双环[3.2.1]辛烷结构的SGLT2抑制剂引起了广泛关注。本研究报道了一种改进的立体选择性合成方法，该方法能够高效地获取该类化合物中最具活性和选择性的化合物之一。通过一锅脱保护/环化反应作为关键步骤，实现了对二氧杂双环[3.2.1]辛烷结构的形成，并完全控制了立体化学。利用适当取代的芳基，该方法能够合成该类化合物中的任意一种。