ACID-CATALYZED CYCLIZATIONS OF N-VINYL-α-SULFINYLACETAMIDES A NOVEL SYNTHETIC APPROACH TO ERYTHRINANE

Article abstract of DOI:10.1016/S0040-4039(00)87302-5

Under the Pummerer reaction conditions, N-(1-cyclohexenyl)-N-methyl-α-(methylsulfinyl)acetamide (7a) cyclized in a 5-endo trigonal fashion through the intermediary cation (8) to give the tetrahydro-4H-oxindole (10).The reaction was successively applied to a novel synthesis of erythrinane skeleton.