Journal
MOLECULES
Volume 23, Issue 3, Pages -Publisher
MDPI
DOI: 10.3390/molecules23030667
Keywords
pheromone; west corn rootworm; Evans methylation; Julia-Kocienski olefination; convergent synthesis
Funding
- National Natural Science Foundation of China [21502151]
- Fundamental Research Funds for the Central Universities [2452017180]
- Northwest AF University [Z111021405]
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A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia-Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24-29% total yield via a six-step sequence. The simple scale-up strategy provides a new way to achieve the asymmetric synthesis of the sex pheromone.
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