Intramolecular ortho photocycloaddition of salicyclic acid derivatives: Multiple-step reaction cascades and their synthetic application

• Applicant: Professor Dr. Thorsten Bach
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2019 to 2022
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 422215986

The project aims at the development of a photochemical reaction cascade and its application to the synthesis of terpene natural products. The cascade reaction will be studied on salicylic acid derivatives and includes in the first step an intramolecular ortho photocycloaddition to a bicyclic octadiene. In two additional steps, compounds with a bicyclo[4.2.0]octane structure are formed by thermal disrotatory ring opening and photochemical disrotatory [4pi] cyclization. In our specific case, simple and easily accessible aromatic substrates will deliver products with a complex, three-dimensional skeleton, which is found in protoilludanes. The reaction cascade will be applied to the synthesis of this class of natural products. Methodology studies, which address all issues of selectivity will serve to meet the challenges posed by the synthetic targets. An enantioselective variant of the described reaction cascade will be developed.

• DFG Programme: Research Grants