Efficient synthesis of (+/-)-erysotramidine using an NBS-promoted cyclization reaction of a hexahydroindolinone derivative.
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]
Lee
Hyoung Ik
HI
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Cassidy
Michael P
MP
Rashatasakhon
Paitoon
P
Padwa
Albert
A
D003500:Cyclization; D004895:Erythrina / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007769:Lactams / Q000737:chemistry
D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D007769:Lactams; C492626:erysotramidine