Synthesis and Cytotoxicity Evaluation of Betulin Cycloolefin Derivatives by Ruthenium-Catalyzed Ring-Closing Metathesis

The combination of ring-closing metathesis with betulin enables the design and synthesis of novel biomolecules representing a library of triterpenoid derivatives for potential pharmacological research. In this work, cyclic olefin betulin derivatives were attempted to be prepared by the combination of ring-closing metathesis with betulin. Dicyclohexyl carbodiimide coupling reaction allowed the transformation of betulin into two types of linear olefin derivatives that have different methylene spacer lengths between the olefin and ester groups. Subsequently, betulin-based cycloolefins were synthesized by ring-closing metathesis using Grubbs first-generation catalyst. The influence of different parameters including solvents, temperature, catalysts, and catalyst loading on ring-closing metathesis was investigated. Cytotoxicity results indicated that these betulin-based olefin derivatives, derived from renewable bioresources, have potential applications in the biomedical field.

Automated summary

The combination of ring-closing metathesis with betulin allows for the synthesis of a library of triterpenoid derivatives for potential pharmacological research. Different types of betulin derivatives were prepared by coupling reactions and subsequent ring-closing metathesis. The resulting betulin-based olefin derivatives showed potential applications in the biomedical field.