Pheromone, 76. Synthese der Enantiomeren von 10-Methyldodecylacetat und 12-Methyltetradecylacetat, chiralen Pheromonkomponenten vonAdoxophyes-Arten (Lepidoptera: Tortricidae)
✍ Scribed by Bestmann, Hans Jürgen ;Frighetto, Rosa T. S. ;Frighetto, Nelson ;Vostrowsky, Otto
- Book ID
- 102366152
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 269 KB
- Volume
- 1990
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Pheromones, 76. Synthesis of the Enantiomers of 10‐Methyldodecyl Acetate and 12‐Methyltetradecyl Acetate, Chiral Pheromone Components of Adoxophyes Species (Lepidoptera: Tortricidae)
From enantiomeric (R)‐(−)‐ and (S)‐(+)‐2‐methylbutyl bromide (3), available by resolution of (R)‐(−)‐phenylglycinol amides of rac‐2‐methylbutanoic acid, and from enantiomeric 6‐methyloctyl bromide (7) the corresponding phosphonium salts were obtained. Wittig olefination yielded the optically active methyl‐branched olefinic THP ethers 12 and 13, hydrolysis, catalytic hydrogenation, and acetylation gave rise to the formation of the chiral title compounds (R)‐(−)‐ and (S)‐(+)‐10‐methyldodecyl acetate (1) and (R)‐(−)‐ and (S)‐(+)‐12‐methyltetradecyl acetate (2).