Short Step Synthesis of Antitumor Natural Products Having Indolo [2, 3α] carbazole as a Common Skeleton

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1. Study toward Indolo [2,3-α] carbazolesImportant building blocks such as 2,2'-biindolyl, 3-acetoxy-2,2'-biindolyl, 1-acetyl-2,3-dihydro-2,2'-biindolyl were prepared by our own new reactions from industrially available chemical, indigo. Utilizing these compounds as starting materials, four short step total synthetic routes to an antibiotic, 6-cyano-5-methoxyindolo [2,3-α] carbazole, were developed.N-Glycosyl 2,2'-biindolyls were also prepared and found to be excellent substrates for producing N-glycosylindolo [2,3-α] carbazoles.Above methods are widely applicable for the syntheses of various kinds of indolo [2,3-α] carbazoles.2. The Chemistry of 1-Hydroxyindoles2,2'-Biindolyl was also prepared through oxidative coupling of lithium 1-methoxyindol-2-yl and converted to indolo [2,3-α] carbazoles which constituted the fifth synthetic route.1-Methoxyindoles are prepared from 1-hydroxyindoles, which are new compounds in indole chemistry. The chemistry of 1-hydroxyindoles was widely examined and found to be rich in a lot of new findings that were not expected from thusfar known indole chemistry.A frontier in indole chemistry is now open.