Table 1.

Some stereospecific syntheses of insect-related semiochemicals.

Semiochemical	Source	Type	Key Conversions/Reactions	Ref.
bombykol	Bombyx mori	Sex pheromone	Ni- and Pd-catalyzed cross coupling reactions	[138]
(Z)-15-methyl-7-nonacosene and (Z)-17-methyl-7-hentriacontene	Eurytoma maslovskii	Sex pheromone	Grignard reaction	[139]
(3S, 5S, 6S)-tetrahydro-6-isopropyl-3,5-dimethylpyran-2-one	Macrocentrus grandii	Sex pheromone	cationic cyclopropyl-allyl rearrangement, diastereoselective alkylation and diastereoselective hydrogenation	[140]
(3Z, 9Z)-cis-6,7-epoxy-3,9-octadecadiene	Ectropis obliqua	Sex pheromone	regioselective dienol epoxidation (sequential ring-opening)	[131]
2E- and 2Z-homofarnesals (6:4 blend)	Callosobruchus chinensis	Sex pheromone	Ando’s Z-selective alkene synthesis	[132]
(R)-Lavandulyl propionate	Dysmicoccus grassii	Sex pheromone	Two-cycle enzymatic transesterification of racemic lavandulol using Porcine pancreas lipase	[46]
10, 14-dimethyl-1-pentadecyl isobutyrate	Euproctis pseudoconspersa	Sex pheromone	Evans’ methylation and C–C bond formation by Julia-Kocienski coupling and Wittig olefination	[129]
(+)-sitophilure	Sitophilus oryzae L. and Sitophilus zeamais M.	Aggregation pheromone	Enzymatic reduction using S. cerevisiae	[130]
(±)-frontalin	Dendroctonus genus	Aggregation pheromone	Double dihydroxylation, mono-cleavage, and acid-catalyzed intramolecular acetalation	[141]
4, 8-dimethyldecanal (four stereoisomers)	Tribolium castaneum	Aggregation pheromone	Organolithium-mediated reaction	[142]