Study On The Total Synthesis Of Indole Alkaloid Arboridinine

This dissertation focus on the application of Mannich reaction to construct the core skeleton of the arboridinine and related total synthesis research.Chapter 1: An overview of arboridinine and the related synthesis research background.Arboridinine,a pentacyclic monoterpene indole alkaloid with a new framework,was initially isolated by Kam group from a plant of the Kopsia genus in 2015.This natural product possesses an unprecedented cage skeleton that includes multiple rings with varying size(6-and 7-membered ring as well as indolenine heterocycle).It also includes two all-carbon quaternary centers as well as a tertiary alcohol.Chapter 2: Introduction of the key reactions used in the synthesis of arboridinine.In the synthetic studies of the arboridinine,there are three key steps in our synthetic strategy: 1.The construction of hexahydrocarbazole derivatives;2.Double Mannich reaction to construct the molecular skeleton;3.Introduction of hydroxyl groups in the molecule by allylic oxidation.At the beginning of our design,we hope that we will be able to construct the molecular skeleton efficiently and complete the synthesis on the basis of some reported methodologies.Chapter 3: Total synthesis of alkaloids arboridinine.We carried out the research of total synthesis of arboridinine.Using a one pot tandem reaction between the tryptophan derivative and hex-4-en-3-one to obtain the hexahydroindazolone.After selectively removing the amino-protecting group,the molecule skeleton was constructed through a double Mannich reaction.Then we used Wittig reaction to construct an exocyclic double bond.Incorporation of the hydroxyl group to the core structure and following requisite functional group transformations are currently ongoing in our laboratory.