Sigillin A,a Unique Polychlorinated Arthropod Deterrent from the Snow Flea Ceratophysella sigillata |
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| Authors: | Dr Witali Schmidt Dr Thies M Schulze Dr Gregor Brasse Dr Edyta Nagrodzka Michael Maczka Prof?Dr Jürg Zettel Prof?Dr Peter G Jones Prof?Dr Jörg Grunenberg Prof?Dr Monika Hilker Ute Trauer‐Kizilelma Ute Braun Prof?Dr Stefan Schulz |
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| Institution: | 1. Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu‐bs.de/schulz/index.html;2. Speichergasse 8, 3150 Schwarzenburg (Switzerland);3. Institut für Analytische und Anorganische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany);4. Institut für Biologie, Freie Universit?t Berlin, Haderslebener Strasse 9, 12163 Berlin (Germany) |
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| Abstract: | 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. |
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| Keywords: | insect repellents isocoumarine natural products organohalogen compounds α ‐vinylation |
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