TRAIL-FOLLOWING IN TERMITES - STEREOSELECTIVE SYNTHESES OF (Z)-3-DODECEN-1-OL, (3Z,6Z)-3,6-DODECADIEN-1-OL AND (3Z,6Z,8E)-3,6,8-DODECATRIEN-1-OL

(Z)-3-Dodecen-1-ol (4), a candidate trail-following semiochemical for several termite species, was synthetized by (Z)-stereoselective reduction of 3-dodecyn-1-ol (8). (3Z,6Z)-3,6-Dodecadien-1-ol (6), which is a structural analogue of 4, was prepared by a reaction sequence in which the key step was the cross-coupling between 5-(tert-butyldimethylsilyloxy)-2-pentyn-1-yl p-toluene-sulfonate (11) and 1-heptyne (12), in the presence of Cul, NaI and K2CO3. Finally, (3Z,6Z,8E)-3,6,8-dodecatrien-1-ol (3), which is a non-species-specific trail-following pheromone of termites, was prepared by a convergent synthesis in which compound 11 and (E)-3-hepten-1-yne (18) were used as key intermediates.