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ChemInform Abstract: Pheromone Synthesis. Part 193. Simple Synthesis of (.+-.)-Stigmolone (8-Hydroxy-2,5,8-trimethyl-4-nonanone), the Pheromone of Stigmatella aurantiaca.

โœ Scribed by Kenji Domon; Kenji Mori


Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
30
Category
Article
ISSN
0931-7597

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โœฆ Synopsis


Pheromone Synthesis. Part 193. Simple Synthesis of (ยฑ)-Stigmolone (8-Hydroxy-2,5,8-trimethyl-4-nonanone), the Pheromone of Stigmatella aurantiaca. -Stigmolone (VIII), which induces the formation of the fruiting body of S. aurantiaca, is synthesized from ketone (I) in 48% overall yield in four steps. -(DOMON, KENJI; MORI, KENJI; Eur. J. Org. Chem.


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The enantiomers of the title compound 1 were synthesized bacterium Stigmatella aurantiaca at a concentration of 0.4ฯช1.0 nM. from the enantiomers of citronellol (2). Both (R)-and (S)-1 induced the formation of the fruiting body of a myxo-