Development of novel synthetic routes toward natural products including heteroatoms

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The main focus of our research in this term of the grant-in-aid (S) is the synthesis of natural products bearing highly complicated structures. We have already developed the aryl-amination reaction using copper catalyst, and this strategy was applied to the total synthehsis of the natural producs, which include duocarmycin and yatakemycin. Ephedradine A and serotobenine was synthesized using the asymmetric C-H insertion reaction. Radical-mediated construction of indole structure was successfully applied to the total syntheses of strychnine, conophylline and aspidophytine. Synthesis of FR901483, lysergic acid, morphine and oseltamivir was also achieved using our original synthetic strategy. Our synthetic methodology is suited for the scaled-up synthesis of the bioactive compounds which can otherwise be collected only scarcely from the nature. To illustrate our synthetic skills, we have prepared about 500mg of yatakemycin. Thus we are strongly confident about the broad contribution of our achievement in organic synthesis.