A stereocontrolled synthesis of (R,Z)- and (R,E)-14-methyl-8-hexadecenals (trogodermal), the sex pheromones of trogoderma species

A stereocontrolled synthesis of (R,Z)- and (R,E)-14-methyl-8-hexadecenals with high stereochemical purity in both absolute and geometrical configurations was achieved by the use of the S_N2 type ring-opening reaction of (S)-β-methyl-β-propiolactone for the construction of the (R)-configurations, adn the cis-addition of diorganocuprate to acetylene adn the S_N2′ type ring-opening reaction of δ-vinyl-δ-valerolactone for the introduction of (Z)- and (E)-double bonds, respectively.