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The asymmetric synthesis of 2-arylcyclohexene derivatives was realized via π-allylpalldium complex generated from 2-arylcyclohexenol derivatives, Pd (0), and (S) -BINAPO. Using this method, (-) -mesembrine, (-) -mesembrane, (+) -crinamine, (-) -haemanthidine and (+) -pretazetine were synthesized. Subsequently, we planed to synthesize indole alkaloids as a chiral form using this method. Thus, the novel procedure for the synthesis of indole skeleton was developed. Treatment of cyclohexenol derivative having the silyloxymethyl group at the 2-position with N-tosyl-ο-bromoaniline in the presence of Pd2dba3·CHCl3 and (S) -BINAPO gave cyclohexenylamine derivative with 84% ee in 76% yield. The siloxymethyl group was converted into the cyanomethyl group and the resulting compound was treated with Pd (OAc) 2 and PMe2Ph to give indole derivative. From this compound, we succeeded in the total synthesis of (-) -dehydrotubifoline and (-) -tubifoline.

yūki gōsei kagaku kyōkaishi/yuuki gousei kagaku kyoukaishi

Palladium-Catalyzed Asymmetric Synthesis of Cyclohexene Derivatives Having the Substituents at the 2-Position and the Application to the Syntheses of the Natural Products.