First Total Synthesis of the Sex Pheromone of the Oleander ScaleAspidiotus nerii: An Unusual Sesquiterpenic Functionalized Cyclobutane

Abstract

The rational choice of a hydroxy protecting group, as shown by molecular modeling studies and experimentally confirmed, is a key issue for the success of the first total synthesis of an unusual sesquiterpenic trisubstituted cyclobutane, with a homoprenylated chain on a sterically congested quaternary carbon at the cyclobutane ring. The structure corresponds to the sex pheromone of the oleander scale and is entirely new as a natural product.