A concise stereoselective approach to the asymmetric syntheses of (S)-ethyl 4-methyloctanoate and its acid, main aggregation pheromones of the genus Oryctes and an important fragrance compounds, is described. The synthesis utilizes the organocatalyzed MacMillan's cross aldol reaction as key step. The synthetic approach outlined permits synthesis of a variety of enantiopure branched methyl unsaturated and saturated fatty acids.
A concise stereoselective approach to functionalized δ-lactone skeleton from monosilylated ethylene glycol as a starting material and its application to the asymmetric total synthesis of (−)-trans-aerangis lactone have been demonstrated. The synthesis utilizes the organocatalyzed MacMillan’s cross aldol reaction as a key step.
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