Total synthesis of (–)-Isodocarpin by a novel nickel-catalyzed decarbonylative reductive cross-coupling

• Applicant: Dr. Sven Christian Richter
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2022 to 2023
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 500290506

In this research project, an efficient synthesis of the pharmacologically active and structurally complex natural product (–)-isodocarpin is to be developed. The key steps of the planned convergent synthesis are on the one hand the still to be developed nickel-catalyzed decarbonylative cross-coupling of a carboxylic acid anhydride with a vinyl iodide and on the other hand a photochemically induced radical cyclization to build up the pentacyclic backbone. In addition, the final step of the synthesis requires a selective C–H oxidation of activated positions in the molecule. The target compound (–)-isodocarpin is supposed to be obtained in about 13 steps, while the shortest synthesis to date was completed in 20 steps. This project combines the development of new synthetic methods with the total synthesis of a diterpenoid.

• DFG Programme: WBP Fellowship
• International Connection: USA
• Host: Professorin Sarah E. Reisman, Ph.D.