Concise syntheses of insect pheromones using Z-selective cross metathesis.
Very short synthetic routes to nine cis-olefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported. These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.
Department of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, 91125, USA.
Myles B
MB
Herbert
Vanessa M
VM
Marx
Richard L
RL
Pederson
Robert H
RH
Grubbs
D000818:Animals; D002384:Catalysis; D007313:Insecta; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry
D009942:Organometallic Compounds; D010675:Pheromones; D012428:Ruthenium