Pheromone activity, effects chirality

In June 1980, I was talking and tasting good wine at Professor Wittko Francke s home near Hamburg, Germany. We talked on olean, and noticed its axial chirality. We became interested in knowing the effect of axial chirality on its pheromone activity. After my return to Tokyo, we started the synthesis of olean enantiomers, as shown in Figure 4.75. 

In most large-scale commercial applications of pheromones, the active pheromone is not chiral, a synthetic achiral pheromone of a similar structure is active enough, or a racemic mixture is used. The synthesis and separation of enantiomers is usually too costly for large-scale use, and if the racemic mixture or achiral substitute is effective, this presents a much more economically feasible pest control method (see Sidebar 4.B). 

In the hydrogenation of p keto esters (R, R) tartaric acid gives the (R) alcohols and the (S, S) tartaric acid gives the (S) enantiomers. Raney nickel is more effective than supported nickel catalysts. It appears that the active catalyst is nickel tartrate which is adsorbed on the catalyst surface and that the sodium bromide is adsorbed on the non-chiral active sites, thus, keeping them from promoting the non-selective hydrogenations. 2,84 -pj is procedure has been used to prepare the chiral intermediate in the synthesis of the Pine Sawfly sex pheromone. ... 

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