Project 110: Biomimetic Total Synthesis of Ergot Alkaloids
Contact Information
Assoc. Prof. Gang CHEN
Email: gchen2018@sjtu.edu.cn
Project Description and Objectives
Ergot alkaloids are typical indole alkaloids with 3,4-fused rings, and natural or semi-synthetic ones were approved for treatment or relief of neurodegenerative diseases. Due to their unique structure and good biological activities, both the biosynthetic and total syntheses of these natural products were widely studied. In particular, the development of transitional metal-catalyzed reaction provided new synthetic strategies for the total syntheses, for example, Heck reaction, allylic reaction and C-H activation. In this project, we proposed the biomimetic strategy using the C-H activation and decarboxylative reaction. The key steps of the synthesis of lysergic acid include indole C4-H olefination and intramolecular decarboxylative Giese reaction, a chiral route by asymmetric decarboxylative allylic reaction will also be investigated; similarly, indole C4-H alkynylation followed by intramolecular decarboxylative coupling with alkyne provided the key precursor of agroclavine. The aim of this project is not only to provide another efficient route of ergot alkaloids in a biomimetic way, but also to prepare lots of ergot alkaloids for further medical chemistry studies.
Eligibility Requirements
Major in chemistry, including chemistry& biochemistry, chemistry & chemical biology.
Main Tasks
Learn about organic chemistry experiments and total synthesis.
Synthesize some structures by the established route.
Explore the following synthetic steps.
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