ChemInform Abstract: Novel Synthetic Approach to (.+-.)-cis-Disparlure — Pheromone of the Female Unpaired Silk-Moth.
✍ Scribed by A. V. Kel'in; O. G. Kulinkovich
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 32 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Novel Synthetic Approach to (±)-cis-Disparlure -Pheromone of the Female Unpaired Silk-Moth. -A novel approach to cis-disparlure (VII) is presented involving the highly diastereoselective addition of isoheptylmagnesium bromide (III) to 2-bromododecanal (II) as the key step. Stereoselective substitution of the hydroxyl group in bromohydrin (IV) by chlorine atom, syn-elimination of the halogen atoms and epoxidation using monoperphthalic acid affords the title pheromone (VII) in 50% overall yield. The corresponding trans-isomer (VIII) is accessible by diastereoselective base-mediated dehydrohalogenation of bromohydrin (IV). -(KEL'IN, A. V.; KULINKOVICH, O.