Divergent Synthesis of Eudesmane Sesquiterpenoids

Demonstrated herein is a streamlined, unified strategy for the asymmetric, protecting-group-free synthesis of seven oxidized eudesmane congeners. A hydroxy-functionalized decalin scaffold bearing two orthogonally reactive olefins is constructed via an enantioselective tandem Michael addition–Aldol sequence, followed by a stereoselective Au(I)-catalyzed Alder-ene cyclization to establish the eudesmane core. Subsequent strategic late-stage hydrogenation and epoxidation enabled short and scalable access to structurally diverse eudesmane congeners, underscoring the platform's broad potential for complex terpenoid synthesis.