Stereoselective synthesis of (3R,4S/3S,4R)-(6E, 10Z)-3,4,7,11-tetramethyltrideca-6,10-dienal (faranal); the trail pheromone of the Pharaoh's ant

Abstract

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.