- Sigillin A, a unique polychlorinated arthropod deterrent from the snow flea ceratophysella sigillata
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The snow flea Ceratophysella sigillata, a winter-active species of springtail, produces unique polychlorinated octahydroisocoumarins to repel predators. The structure of the major compound, sigillin A, was elucidated through isolation, spectroscopic analysis, and X-ray crystallography. Sigillin A showed high repellent activity in a bioassay with predatory ants. A promising approach for the total synthesis of members of this new class of natural compounds was also developed. Inedible: The snow flea Ceratophysella sigillata produces unique polychlorinated octahydroisocoumarins to repel predators. The structure of the major representative, sigillin A, was elucidated through isolation, spectroscopic analysis, and X-ray crystallography. A promising synthetic approach for the total synthesis of this class of compounds was developed, in which α-vinylation of a lactone and ring-closing metathesis are the key steps. (Image: F. Kohl)
- Schmidt, Witali,Schulze, Thies M.,Brasse, Gregor,Nagrodzka, Edyta,Maczka, Michael,Zettel, Jürg,Jones, Peter G.,Grunenberg, J?rg,Hilker, Monika,Trauer-Kizilelma, Ute,Braun, Ute,Schulz, Stefan
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