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Faranal (1), the trail-following pheromone of the worker of Pharaoh's ant (Monomorium pharaonis), was synthesized by the coupling reaction of the iododiene 3 with the chiral building block 8 as the key step. The geometrically pure iododiene 3 was prepared by the zirconocene-mediated carboalumination reaction of 2 followed by treatment with iodine.

(3 S 4 R )-(+)-Faranal and its antipode were synthesized. The former was comparable in bioactivity with that of the natural pheromone.

(+)-Faranal 1a , the trail pheromone of Pharaoh's ant, and its congener, (+)-13-norfaranal 1b were synthetized from chiral building block 4 employing diastereoselective carbon-carbon bond formation. The application of crude pig liver esterase enzyme for the preparation of 4 is also discussed.

(+)-Faranal 1 , the trail pheromone of Pharaoh's ant, was synthesized in 10 % overall yield starting from an easily available chiral building block 2 and employing diastereoselective carbon—carbon bond formation.

(+)-Faranal 1 , the trail pheromone of Pharaoh's ant, was synthesized in 10 % overall yield starting from an easily available chiral building block 2 and employing diastereoselective carbon—carbon bond formation.

The ability of ants to reacting to sublethal high temperatures with production of gynandromorphs is reported for the first time. The abnormal forms produced in the pharaoh's ant range from ergatandromorphs to classical halfsidegynanders.

Racemic (3S,4R/3R,4S)-faranal [(1a)+(1b)] has been synthesised by a convergent, stereospecific route which employed the addition of alkylcopper complexes to terminal acetylenes, to generate two trisubstituted double bonds, and a Diels–Alder reaction to establish the relative stereochemistry of the C-3, C-4 methyl groups. A diastereoisomeric mixture of faranals, enriched in the (3S,4S/3R,4R)-enantiomeric pair [(1c)+(1d)], has been synthesised by a somewhat shorter route via an intermediate diester, obtained from electrochemical dimerisation of ethyl crotonate.

Recemic (3R, 4S/3S, 4R)-faranal, has been synthesised by a convergent, stereospecific route from (1E, 5Z)-1-iodo-2, 6-dimethylocta-1,5-diene in good overall yield; this synthesis employed the addition of alkylcopper complexes to terminal acetylenes to generate the two trisubstituted double bonds, and a Diels–Alder reaction to establish the relative configuration of the C-3, C-4 methyl groups.