Synthetic studies on antitumor active molecules utilizing of sequential cyclizations

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The synthetic studies on several antitumor active compounds including δ-tocotrienol, coriolin and paclitaxel were performed. The following results, 1) to 4), were provided by this study. 1) A novel and short step synthetic route for δ-tocotrienol was developed. 2) In the course of the synthetic studies on coriolin, samarium (II) iodide-induced cascade reaction involving reductive coupling-Dieckmann condensation of bis-α, β-unsaturated esters bearing tert-butyldimethylsilyloxy group at δ-position to highly diastereo- and regioselectively produce bicyclo [3. 3. 0] octane ring systems in optically active form. 3) A stereoselective and efficient synthetic route for the C ring system of paclitaxel was developed. 4) Cascade reaction involving reductive cyclization, Dieckmann condensation, and lactonization of E- and Z-dimethyl 2-methyl-8-oxoundec-2-enedioates and Z-dimethyl 2-methyl-7-oxodec-2-enedioate with samarium (II) iodide was found to stereospecifically produce cis and trans bicyclo [4. 4. 0] decane ring systems and trans bicyclo[4.3.0]nonane ring system each consisting of γ-lactone, respectively.