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Two-step synthesis of (±)-stigmolone, the pheromone of Stigmatella aurantiaca

✍ Scribed by Oleg L Epstein; Oleg G Kulinkovich

Book ID
104230630
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
58 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Racemic stigmolone (8-hydroxy-2,5,8-trimethyl-4-nonanone), the pheromone of myxobacterium Stigmatella aurantiaca, was synthesised in 67% overall yield, using titanium-mediated hydroxycyclopropanation of 2-methyl-5-hexen-2-ol with ethyl isovalerate followed by the base-induced ring opening of the resulting 2-(3-hydroxy-3-methylbutyl)-1-isobutyl-1-cyclopropanol.

📜 SIMILAR VOLUMES

ChemInform Abstract: Pheromone Synthesis
ChemInform Abstract: Pheromone Synthesis. Part 193. Simple Synthesis of (.+-.)-Stigmolone (8-Hydroxy-2,5,8-trimethyl-4-nonanone), the Pheromone of Stigmatella aurantiaca.
✍ Kenji Domon; Kenji Mori 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

Pheromone Synthesis. Part 193. Simple Synthesis of (±)-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.