4.3 Article

A New Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth

Journal

NATURAL PRODUCT COMMUNICATIONS
Volume 16, Issue 5, Pages -

Publisher

SAGE PUBLICATIONS INC
DOI: 10.1177/1934578X211020149

Keywords

14-methyl-1-octadecene; pheromone synthesis; Peach Leafminer Moth; Chiral-pool strategy

Funding

  1. NSFC [31301712, 31760639]
  2. Jiangxi Technological Normal University
  3. Opening Funds of the Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry
  4. Chinese Academy of Sciences

Ask authors/readers for more resources

The asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth, has been efficiently achieved, with a key chiral intermediate obtained in large quantities from the steroid industry. Selective masking and conversion into a phosphonium salt derivative were used to construct the carbon skeleton, with the target molecule synthesized in 8 linear steps and a 42% yield. The key characteristic of this synthesis lies in its chiral-pool strategy.
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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.3
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available