Cedrane sesquiterpenes possess common tricyclo[5.3.1.01,5]undecane core structure.The varied oxa-five-membered ring decorating their core structure to form 8-oxa-tetracyclo[7.2.2.01,5.06,13]tridecane framework,containing six consecutive chiral centers (including two all-carbon quaternary centers and one oxygenated quaternary carbon center),has proven to be a synthetic challenge and a bio-synthetic mystery to date.Herein,we reported a distinct and biomimetic strategy to these sesquiterpenes resulting in the concise asymmetric total syntheses of three cedrane sesquiterpenes from simple commercially available building blocks.Key feature is ex-ploitation of a cascade oxidative dearomatization-induced[5+2]cycloaddition/etherification to highly stereocontrolled construct 8-oxa-tetracyclo[7.2.2.01,5.06,13]tridecane framework with five contiguous chiral centers in one step.In addition,a metal-free i2-catalyzed and DMSO-mediated oxidative dehydroaromatization was applied to prepare curcuphenol and its derivatives from the highly functionalized cyclohexenones with minimal manipulations.