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Synthesis 2000; 2000(13): 1848-1851
DOI: 10.1055/s-2000-8219
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First Asymmetric Synthesis of Stigmolone: The Fruiting Body Inducing Pheromone of the Myxobacterium Stigmatella Aurantiaca

Dieter Enders* , André Ridder
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany; Fax + 49(2 41)8 88 81 27; E-mail: Enders@RWTH-Aachen.de
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Publication Date:
31 December 2000 (online)

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The asymmetric synthesis of (S)- and (R)-stigmolone [(S)- and (R)-1], an aggregation pheromone of the myxobacterium Stigmatella aurantiaca, starting from 4-methylpentan-2-one is described. The stereogenic centre at the C-5 position of the pheromone was generated via the SAMP/RAMP hydrazone method with high enantiomeric purity. It could be shown again that both enantiomers induce the fruiting body formation of the myxobacterium at concentrations of 1.0-30.0 nM.

asymmetric synthesis - pheromones - hydrazones - natural products - Stigmatella aurantiaca