9-Methyl-12-carbaeudistomin (1, 13b-cis-1-amino-13-methyl-1, 2, 3, 4, 7, 8, 13, 13b-octahydro[1', 2']oxazepino-[2', 3', : 1, 2]pyrido[3, 4-b]indole) (2), which has a carbon atom instead of the sulfur atom in the D-ring of tetracyclic eudistomins (1), its 1, 10-trans isomer (3), and their 11, 12-didehydro derivatives (4 and 5) were synthesized from 2-vinylazetopyridoindoles (8 and 17) via the [2, 3]-Meisenheimer rearrangement of the corresponding N-oxides, for structure-activity relationship study of edistomins (1). Similarly, 5-amino-3, 6-epoxyhexahydroazocino[5, 4-b]-indoles (6 and 7) were synthesized from 2-ethylazetopyridoindole (33) via the [1, 2]-Meisenheimer rearrangement of the corresponding N-oxide.