Selective functionalization of 1,2-dihydronaphthalenols leads to a concise, stereoselective synthesis of sertraline

Article abstract of DOI:10.1016/S0040-4020(99)00456-1

Asymmetric reductive ring opening of oxabenzonorbornadiene provides dihydronaphthalenols in high ee and good yield. Functionality present in this system can be used to elaborate the core towards a number of targets. As an illustration, a concise stereoselective synthesis of the important antidepressant sertraline is described.