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Efficient Synthesis of (±)-Erysotramidine Using an NBS-Promoted Cyclization Reaction of a Hexahydroindolinone Derivative

2003; American Chemical Society; Volume: 5; Issue: 26 Linguagem: Inglês

10.1021/ol036106r

1523-7060

Hyoung Ik Lee, Michael P. Cassidy, Paitoon Rashatasakhon, Albert Padwa,

Synthesis and Biological Activity

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]