Collective Asymmetric Total Syntheses Of Iboga-Type Indole Alkaloids

This thesis was mainly focused on the asymmetric total syntheses of(+)-Tabertinggine,which was used as the key intermediate of the collective synthesis of iboga-type monoterpene indole alkaloids,and collective total synthesis research of these alkaloids.It consisted of the following three chapters:Chapter 1 The Application of Pictet-Spengler Reaction in the Synthesis of Alkaloid(review)This review briefly described the application of the Pictet-Spengler reaction in the synthesis of alkaloids,which presented the important role of Pictet-Spengler reaction in the construction of alkaloid framework.Chapter 2 Asymmetric Total Synthetic Research of Iboga-type Indole Alkaloid(+)-TabertinggineA brief introduction of the background for the isolation,structures and biological activities of iboga-type indole alkaloids were provided.The asymmetric synthesis of the key intermediate(+)-Tabertinggine was completed with high enantioselectivity using substrate-induced and chiral phosphoric acid catalyzed strategies respectively,which laid a foundation for the collective synthesis of these natural products.Chapter 3 Collective Total Synthesis of Iboga-type Indole AlkaloidsIn this chapter,the synthesis research progress of Catharanthine-type Iboga alkaloids was briefly introduced,the idea of collective synthesis of Iboga alkaloids through the common key intermediates was proposed.The construction of key intermediates had experienced three strategies,The first strategy was based on the initial construction of intramolecular amidation and then the construction of C2-C16 bond,The second strategy was based on the construction of C2-C16 bond firstly and followed by the construction of molecular lactam,The third strategy was based on the classical Pictet-Spengler reaction and the following rearrangement to complete the construction of the key intermediates.