Development of a Highly Modular Synthesis of the Novel Anti-Influenza Natural Products Wickerol A and B

• Applicant: Dr. Matthias Göhl
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2016 to 2019
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 329049264

There is neither a total synthesis of the potent antiviral wickerols A and B, nor of suitable model systems known to date. As these structures are very promising potential pharmacophores for further anti-influenza structure activity relationships investigations, we would like to develop a synthetic approach to access this kind of compounds in this project. As both interesting diterpenes have a novel fused 6-5-6-6 complex cage structure, they seem challenging to prepare. The key transformations include a [2,3]-Wittig anionic oxy-Cope rearrangement cascade followed by a type II ring-closing carbonyl-ene reaction to establish the last axial-faced carbocycle with functionalizations in the right place. Essentially, our main focus is to outline short synthetic strategy that is highly modular and allows late-stage diversification for promising SAR studies.

• DFG Programme: Research Fellowships
• International Connection: USA
• Host: Professor Christopher Vanderwal, Ph.D.