Cryptolestes pusillus

Advent of ring-closing olefin metathesis reaction has influenced the synthetic strategy of pheromones very much. For example, the racemate of a macrolide pheromone such as (5Z,13S)-5-tetradecen-13-olide (29) (aggregation pheromone of the flat grain beetle, Cryptolestes pusillus) could readily be synthesized as shown in Scheme 42 [67]. Unfortunately, ( )-29 prepared by this method was a mixture of c/s, trans-isomers (Z/E=69 31). (S)-5-Hexadecanolide (27) was also synthesized by means of ring-closing olefin metathesis as shown in Scheme 43 [68]. 

A. V. (1985). Aggregation pheromones of the flat grain beetle, Cryptolestes pusillus (Coleoptera Cucujidae). J. Chem. Ecol. 11, 1053-1070. 

Figure 3.38 Macrocyclic lactones from beetle aggregation pheromones. Compound A is found in Cryptolestes pusillus, the flat grain beetle, compounds Band E in C. surinamensis, a mixture of enantiomers of C in C. turcicus, compound D and the R-enantiomer of E in C. ferrugineus, the rusty grain beetle...

Some macrolides are used as aggregation pheromones. Ferralactones I (= cucu-jolide 1,155) and II (156) are 11- and 12-membered ring macrolides, respectively, produced by the rusty grain beetle Cryptolestes ferrugineus [182]. (Z)-3-Dodecen-12-olide (157) and cucujolide HI (158) are 13- and 14-membered ring macrolides, respectively, produced by C. pusillus and C. turcicus, respectively [183,184]. 

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