Synthesis of Optically Pure (1S, 4S, 5S)-2-Pinen-4-ol (cis-Verbenol) and Its Antipode, the Pheromone ofIpsBark Beetles
- 1 August 1976
- journal article
- research article
- Published by Oxford University Press (OUP) in Agricultural and Biological Chemistry
- Vol. 40 (8), 1611-1615
- https://doi.org/10.1080/00021369.1976.10862248
Abstract
The enantiomers of cis-verbenol (4a and 4a′) were first synthesized in optically pure state. (1S, 4S, 5S)-2-Pinen-4-ol (4a′) was dextrorotatory in acetone or in methanol but it was levorotatory in chloroform; cis-verbenols are indistinguishable by a prefix (+) or (−). The designation of the Ips pheromone as (+)-cis-verbenol is therefore ambiguous and it should be called as (1S, 4S, 5S)-2-pinen-4-ol (4a′) or (S)-cis-verbenol.This publication has 3 references indexed in Scilit:
- Synthesis of Optically Pure (+)-trans-Verbenol and Its Antipode, the Pheromone ofDendroctonusBark BeetlesAgricultural and Biological Chemistry, 1976
- Synthesis of the principal components of the sex attractant from male Ips confusus frass: 2-methyl-6-methylene-7-octen-4-ol, 2-methyl-6-methylene-2,7-octadien-4-ol, and (+)-cis-verbenolTetrahedron, 1968
- Methodology for Isolation and Identification of Insect Pheromones with Reference to Studies on California Five-Spined Ips1Journal of Economic Entomology, 1967