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An efficient asymmetric synthesis of (4 R ,8 R )‐4,8‐dimethyldecanal, the most active component of natural Tribolure
Author(s) -
Shi Jianmin,
Wei Liang,
Liu Lu,
Tang Meng,
Zhang Tao,
Bai Hongjin,
Du Zhenting
Publication year - 2019
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201800381
Subject(s) - chemistry , component (thermodynamics) , yield (engineering) , stereochemistry , optically active , combinatorial chemistry , organic chemistry , materials science , physics , metallurgy , thermodynamics
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.