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An efficient asymmetric synthesis of (4R,8R)‐4,8‐dimethyldecanal,the most active component of natural Tribolure
Authors:Jianmin Shi  Liang Wei  Lu Liu  Meng Tang  Tao Zhang  Hongjin Bai  Zhenting Du
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.
Keywords:aggregation pheromone  chiral‐pool strategy  synthesis
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