title: Efficient synthesis of (+/-)-erysotramidine using an NBS-promoted cyclization reaction of a hexahydroindolinone derivative.
abstract: An NBS-promoted intramolecular electrophilic aromatic substitution reaction of a hexahydroindolinone derivative was used to assemble the tetracyclic core of the erythrinane skeleton. The resulting cyclized product was transformed into (+/-)-erysotramidine in three additional steps. The cyclization reaction is also successful using variously substituted aryl and furanyl bicyclic lactams under acidic conditions. [reaction: see text]
authors.affiliation: Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
authors.forename: Hyoung Ik
authors.initials: HI
authors.lastname: Lee
authors.forename: Michael P
authors.initials: MP
authors.lastname: Cassidy
authors.forename: Paitoon
authors.initials: P
authors.lastname: Rashatasakhon
authors.forename: Albert
authors.initials: A
authors.lastname: Padwa
mesh_terms: D003500:Cyclization; D004895:Erythrina / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007769:Lactams / Q000737:chemistry
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D007769:Lactams; C492626:erysotramidine