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

Abstract

An asymmetric synthesis of (4R,8R)‐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, (4R,8R)/(4R,8S)/(4S,8R)/(4S,8S), and their ratio is 4/4/1/1. However, the (4R,8R)‐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.