Enantiospecific Synthesis of Both Enantiomers of the Longtailed Mealybug Pheromone and Their Evaluation in a New Zealand Vineyard

The
irregular monoterpenoid sex pheromone of Pseudococcus
longispinus and its enantiomer were prepared from the corresponding
bornyl acetates. The use of readily accessible chiral starting materials
and lactone–lactone rearrangement are the highlights of the
present synthesis. The biological activities of the two enantiomers
and racemic mixture were tested in a New Zealand vineyard. The (S)-(+)-enantiomer was significantly more attractive to P. longispinus males than the racemic mixture or the (R)-(−)-enantiomer.