Manica mutica

Conversely, Bestmann and coworkers utilized the Rupe reaction to prepare normanicone , a mandibular gland pheromone in the North American ant species manica mutica and manica bradley. In a manner similar to above, acetylide addition produced alcohol 44 which was treated with P2O5 to yield the Rupe product 45, albeit in low yield. 

In a similar manner, the alicyclic precursor of multistriatin may be 4,6-dimethyl-7-octen-3-one (301, Scheme 55). Similar compounds have been obtained in alarm and defensive secretions of certain insects. Pales et al. (451) found that the mandibular gland secretion of the ant Manica mutica contained mainly 4,6-dimethyl-4-octen-3-one. Meinwald et al. (452) identified 4,6-dimethyl-6-octen-3-one in the defensive secretion of the daddy long legs, Leiobunum vittatum. 

---