Synthesis of (4R,8R)- and (4S,8R)-4,8-dimethyldecanal:: the common aggregation pheromone of flour beetles

The synthesis of (4R,8R)- and (4S,8R)-4,8-dimethyldecanal 1 and la has been achieved connecting the chiral building block (R)-2-methyl-l-bromobutane 4 with (R)- and (S)-citronellol derivatives. The key intermediate 4 was obtained optically pure in five steps from methyl (S)-3-hydroxy-2-methylpropionate 2. (c) 2006 Elsevier Ltd. All rights reserved.