Total Synthesis of Mersicarpine Through a Cationic Cyclization Approach.
2014
A concise total synthesis of mersicarpine is achieved by exploiting a cyclic carbamate for generation of a tertiary carbocation. The key step involves intramolecular Friedel–Crafts alkylation with this carbocation for the construction of a quaternary carbon center and a subsequent oxidation and cyclization cascade for the formation of a seven-membered cyclic imine. The chemistry allowed for a rapid one-pot synthesis of mersicarpine from a simple intermediate using straightforward chemical operations.
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