Aphthona flea beetles, sesquiterpene

Bartelt, R.J., Cosse, A.A., Zilkowski, B.W., Weisleder, D. andMomany, F.A. (2001). Male-specific sesquiterpenes from Phyllotreta and Aphthona flea beetles. J. Chem. Ecol., 27, 2397-2423. 

Male ptoduced phetotnone candidates of the flea beetle Aphthona Flava, which wete four himachalene type sesquiterpenes were synthesized from (i )-(+)-citronellal and their stereochemistry discussed. However, there is some ambiguity regarding the stereochemistry. ... 

Bartelt, R. J., Weisleder, D. and Momany, F.A. (2003). Total synthesis of himachalene sesquiterpenes of Aphthona and Phyllotreta flea beetles. Synthesis, 2003, 117-123. 

Muto, S., Bando, M. and Mori, K. (2004). Synthesis and stereochemistry of the four himachalene-type sesquiterpenes isolated from the flea beetle (Aphthona flava) as pheromone candidates. Eur. J. Org. Chem., 2004,1946-1952. 

Semiochemicals are usually compounds with structures much simpler than that of brevenal. But even with simple compounds, there are possibilities of misassigning their absolute configuration. Male-produced pheromone components of the flea beetle Aphthona flava were isolated and identified in 2001 by Bartelt etal6 They proposed himachalene-type sesquiterpene structures 2—5 (Figure 2) to the components. In 2004, Mori and coworkers synthesized 2-5 and their enantiomers ent-2—mt-S from enantiomers of citronellal, and the... 

In 2001, Bartelt et al. in the USA isolated and identified four himachalene-type sesquiterpenes (A-D, Figure 4.23) as the male-produced aggregation pheromone of the flea beetle (Aphthona flava). In order... 

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