Acalymma vittatum

Two recent examples of isolation are gentisyl quinone isovalerate [185] and a novel p-lactone, vittatalactone [(3R,4R)-3-methyl-4-(l,3,5,7-tetramethyloctyl)oxetan-2-one [118]. The fornier is a female sexual pheromone which was isolated from the German cockroach Blattella germanica), and the latter is an aggregation pheromone which was isolated from collections of airborne volatile compounds from feeding male striped cucumber beetles, Acalymma vittatum. 

Acalymma vittatum (Fabricius) Callosobruchus chinensis Linnaeus Callosobruchus maculatus (Fabricius)... 

Many arthropod pheromones are of putative polyketide origin, which are discussed in greater detail in Chapter 4.04. One noteworthy example is the novel 2,3-disubstituted /3-lactone, vittatalactone (73), recently characterized as a suspected male-produced aggregation pheromone for the striped cucumber beetle, Acalymma vittatum Vittatalactone is the first /3-lactone to be isolated from a beetle, and is only the third such structure to be characterized from an insect (Figure 24). 

Figure 24 Vittatalactone (73) from the striped cucumber beetle, Acalymma vittatum.

Vittatalactone [105] Vittatalactone (192) is a pheromone isolated in 2005 from the striped cucumber beetle Acalymma vittatum [103]. This natural product presents a unique structure bearing a trawi-p-lactone and a deoxypropionate side chain. In 2009, Breit and coworkers assigned both its relative and absolute configurations [104]. 

An enantioselective total synthesis including an HNL-catalyzed step of the pheromone vittatalactone, a novel P-lactone originally isolated from feeding male striped cucumber beetles, Acalymma vittatum was recently published. PaHNL catalyzes with high enantioselectivity (>96% ee) the formation of the (R)-cyanohydrin from crotonaldehyde 9 a key step in the synthesis of one of the two main building blocks 11 (Scheme 28.5). ... 

Morris BD, Smyth RR, Foster SP, Hoffmann MP, Roelofs WL, Franke S, Francke W. Vittatalactone, a p-lactone from the striped cucumber beetle, Acalymma vittatum. J. Nat. Prod 2005 68 26-30. 

---