Anthonomus grandis Grandisol

Scheme 54 summarizes Font s synthesis of (+)-grandisol (36), the male pheromone of the cotton boll weevil (Anthonomus grandis) [80]. The key-step is the double [2+2] photocycloaddition of ethylene to bis(a,(3-butenohde) A to give B, which yielded C after glycol cleavage. The recently identified pheromone of the oleander scale (Aspidiotus nerii) possesses a structure similar to that of grandisol (Scheme 54), and its synthesis was reported by Ducrot [81 ] and also by Guerrero [82,83]. 

Dickens J. C. and Mori K. (1989) Receptor chirality and behavioral specificity of the boll weevil, Anthonomus grandis Boh. (Coleoptera Curculionidae), for its pheromone, (+)-grandisol. J. Chem. Ecol. 15, 517-528. 

Grandisol (8), one of the synergistic mixture of the four compounds (collectively called grandlure ) of sex pheromones of male boll weevil (Anthonomus grandis) has been synthesized by the following two-step procedure (Eq. 7)47). Racemic grandisol... 

C,oH,sO, Mr 154.25, oil, bp, 50-60°C (133 Pa), 22.1° (hexane). Sexual pheromone of the male boll weevil (Anthonomus grandis). G. is also a component of the pheromone system of bark beetles of the genus Pityophthorus. In addition it forms, together with the aldehyde (grandisol, C oH jO, Mr 152.24), the aggregation pheromone of weevils of the genus Pis-sodes. 

Chrysanthemic acid is a monocyclic terpene containing a three-membered ring. Its esters are found in the flower heads of pyrethrum (Chrysanthemum cinerariaefolium) and are naturally occurring insecticides. A cyclobutane is present in grandisol, the sex-attracting chemical nsed by the male boll weevil (Anthonomus grandis). 

The ten farnesylacetone derivatives isolated from Cys-tophora moniliformis are individual insofar as there are several types of carbon skeleton, particularly that of pyro-nane (1,1,2,3-tetramethylcyclohexane). However, the most original compound is probably the one that has the rare cyclobutanic system of grandisol, a sex pheromone of the male boll weevil Anthonomus grandis (Tumlinson et al, 1969). 

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