An efficient asymmetric synthesis of (4 R ,8 R )‐4,8‐dimethyldecanal, the most active component of natural Tribolure

An asymmetric synthesis of (4 R ,8 R )‐4,8‐dimethyldecanal, the most active component of natural tribolure , was achieved through an asymmetric methylation as a key step and chiral‐pool strategy. Natural tribolure is a mixture of four stereoisomers, (4 R ,8 R )/(4 R ,8 S )/(4 S ,8 R )/(4 S ,8 S ), and their ratio is 4/4/1/1. However, the (4 R ,8 R )‐isomer is the most active one. Based on a chiral‐pool strategy, we used a recycled chiral molecular ( R )‐4‐(Benzyloxy)‐3‐methylbutanal that we exploited in our previous article. After executing a C5 + C5 + C2 synthetic plan, the target molecule was obtained in nine linear steps and in 36.8% overall yield.