title: Total synthesis of mersicarpine through a cationic cyclization approach.
abstract: 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.
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin, China , 300071.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Lv
authors.forename: Zining
authors.initials: Z
authors.lastname: Li
authors.forename: Guangxin
authors.initials: G
authors.lastname: Liang
mesh_terms: D000478:Alkylation; D029062:Apocynaceae / Q000737:chemistry; D002384:Catalysis; D002412:Cations; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D002412:Cations; D026121:Indole Alkaloids; C529544:mersicarpine