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Huang, Nan

Chemistry

2007

MS

The project of this thesis involves the total synthesis of (±)-Catharanthine via a novel Diels-Alder reaction developed for the synthesis of the iboga alkaloids compound family. Some congeners of catharanthine have displayed anti-addiction activities, which is important for developing new and safe treatment of drug addiction. In order to obtain various analogue of catharanthine we have to develop a general synthetic methodology which can be applied for the total synthesis of the natural product family. A novel Diels-Alder reaction was successfully proved as key for the synthesis of a tetracyclic compound which is a common precursor and thus can be used for the synthesis for the catharanthine alkaloid family. In this project, the total synthesis was successfully completed with the product which is identical to racemic catharanthine. The result of this project proved that the intramolecular Diels-Alder reaction could be used for the total synthesis of the iboga alkaloid natural product family. With the slight modification of the protecting group, the intramolecular reaction could end up with a chiral product, which can be further used for the synthesis of the chiral natural product.