Efficient synthesis of (±)-erysotramidine using an NBS-promoted cyclization reaction of a hexahydroindolinone derivative

HI Lee, MP Cassidy, P Rashatasakhon, A Padwa

Index: Lee, Hyoung Ik; Cassidy, Michael P; Rashatasakhon, Paitoon; Padwa, Albert Organic letters, 2003 , vol. 5, # 26 p. 5067 - 5070

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Citation Number: 29

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.