SYNTHESIS OF BOTH THE ENANTIOMERS OF LARDOLURE, THE AGGREGATION PHEROMONE OF THE ACARID MITE, LARDOGLYPHUS KONOI

Article abstract of DOI:10.1016/S0040-4020(01)88157-6

Both the enantiomers of lardolure were synthesized in 100 percent optical purity and 99.6 percent diastereomeric purity by use of Frater's diastereoselective alkylation as the key-step.Since (1R,3R,5R,7R)-enantiomer showed the same ORD sign and bioactivity as those shown by the natural pheromone, the structure of lardolure was established unambiguously as (1R,3R,5R,7R)-1,3,5,7-tetramethyldecyl formate.