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- Title
A New Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth.
- Authors
Guo-Guo He; Si-Fan Liu; Bao-Qi Rao; Hong-Jin Bai; Zhen-Ting Du
- Abstract
An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth, has been efficiently achieved. A key chiral intermediate, (R)-4-(benzyloxy)-3-methylbutanal, which has been developed as the resource chemical, can be obtained in large quantities from the steroid industry. 1,11-Undecanediol is selectively masked, and then converted into a phosphonium salt derivative, thereby effectively constructing a carbon skeleton. The target molecule is synthesized in 8 linear steps, with a 42% yield. The key characteristic of our synthesis lies in its chiral-pool strategy.
- Subjects
PHEROMONES; LEAFMINERS; STEROIDS; CHIRAL drugs; CHEMICALS
- Publication
Natural Product Communications, 2021, Vol 16, Issue 5, p1
- ISSN
1934-578X
- Publication type
Article
- DOI
10.1177/1934578X211020149