Methyldodecyl acetate

One further application is the synthesis of (S)-l-methyldodecyl acetate, the pheromone of Drosophila mulleru by a deprotonation/methylation sequence starting with 1 -dodecanol in 59 % overall yield and very high enantioselectivity (98% ee)43. 

S)-l-Methyldodecyl acetate, a Drosophila pheromone (-)-sparteine assisted enantioselective lithiation8... 

An early demonstration, reported by Hoppe, of the use of sparteine for the generation of dipole-stabilized carbanions and their subsequent application in asymmetric synthesis involves carbamates such as 37 (Scheme 13.5) [48], The synthesis of the Drosophila mulleri pheromone (S)-l-methyldodecyl acetate (39) illustrates the features of this process. This approach was also employed with substrate 40 (> 95 % ee), which could be sequentially metalated and functionalized to give 42 (dr >97 3) as shown in Scheme 13.6 [49]. 

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