ISSN:
0170-2041
Keywords:
Pheromones
;
Adoxophyes spp.
;
10-Methyldodecyl acetate
;
12-Methyltetradecyl acetate
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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).
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1990199001155
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