Synthesis of 2-Fluoro Analogues of Frontalin (original) (raw)

The synthesis of enantio- and diastereomerically pure 2-fluoro analogues of the aggregation pheromone frontalin is reported. Key to the process is the preparation of a chiral, α-fluorosubstituted oxirane, which serves as an important intermediate. A series of nucleophilic substitutions and reactions lead to the final 2-fluoro analogue of frontalin, confirming the successful selective replacement of hydrogen atoms with fluorine, advancing the understanding of frontalin's derivatives and their potential biological relevance.