Quick access to the core of mersicarpine through an SNAr strategy

Abstract: A quick access to the core of dihydroindole alkaloid mersicarpine was developed based on straightforward transformations from readily available and inexpensive starting materials. The synthetic route features an aldol reaction, a Beckmann rearrangement for the synthesis of the δ-lactam, an intramolecular SNAr strategy for indoxyl heterocycle formation, and in situ autoxidation of indoxyl intermediate. The new strategy offered an alternative approach for the formation of an oxidized indoxyl moiety, which could potentially have a wider application in the total synthesis of indole alkaloids containing apparent or masked indoxyl moieties. [Copyright &y& Elsevier]