合成路线1

Ethyl 5-hydroxy-2-methylindole (I) was dimethylated with iodomethane in the presence of KH to give (II). Nitration of (II) in AcOH afforded the 4-nitroindole (III) together with some 6-nitro isomer (IV), which were separated by column chromatography. Reduction of (III) with Sn and HCl yielded the 4-aminoindole (V). This was then oxidized with Fremy's salt to afford the corresponding indolequinone (VI) (1). Quinone (VI) was reduced to the hydroquinone (VII) with sodium dithionite, and this was further reduced with DIBAL-H to give, after oxidative work-up with FeCl3 to regenerate the quinone, the 3-(hydroxymethyl) indolequinone (VIII). Finally, substitution of the methoxy group of (VIII) with aziridine (IX) in DMF yielded the target compound (2).