Synthetic Studies on Biologically Active Poly-Functionalized Carbazoles

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1. The free radical scavenger carazostatin and the marine alkaloid hyellazole have been synthesized by a new type of allene-mediated electrocyclic reaction involving the indole 2,3-bond as a key step.2. New tetracyclic oxazolo [4,5-c] carbazole and oxazolo [5,4-c] carbazole ring systems as functionalized precursors to antioxidative antiostatins (A_<1-4> and B_<2-5>) and carbazoquinocins (A-F) were synthesized.3. A new benzo-annelation method based on the allene-mediated electrocyclic reaction of 2,3-functionalized indoles provides an effective route to the highly-functionalized carbazole ring, and the total syntheses of carazostatin, hyellazole and carbazoquinocins B to F have been completed. Moreover, the first total syntheses of carbazoquinocins B,C,E and F were demonstrated.