A concise synthesis of herbertenolide.

A concise synthesis of (±)-herbertenolide has been accomplished herein. The strategy relies on a H 2 O 2 -mediated oxidative ring contraction of all-substituted cyclic α-formyl ketones for the stereospecific construction of contiguous quaternary carbon centers (CQCCs). Furthermore, a Sc(OTf) 3 /chiral N , N '-dioxide catalyzed asymmetric Michael addition of benzofuranone to MVK has been optimized for forging a chiral aromatic quaternary carbon center, which enables the formal synthesis of (+)- ent -herbertenolide.