Synthesis of the enantiomers of lasiol, an acyclic monoterpene alcohol in the mandibular gland secretion of the male ants, Lasius meridionalis.
(2S,3S)-(-)-Lasiol (2,3,6-trimethyl-5-hepten-1-ol, 1) and its antipode were synthesized from cis-4,5-dimethylcyclohexene oxide (3) by employing asymmetric cleavage of the epoxy ring with a chiral lithium amide derived from 4 to give optically active cis-4,5-dimethyl-2-cyclohexen-1-ol (5) as the key-step.
Kasai
T
T
Department of Agricultural Chemistry, University of Tokyo, Japan.
Watanabe
H
H
Mori
K
K
D000438:Alcohols / Q000138:chemical synthesis*; D000818:Animals; D001000:Ants / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008334:Mandible; D012724:Sex Attractants / Q000138:chemical synthesis; D013237:Stereoisomerism
D000438:Alcohols; D012724:Sex Attractants; C089338:lasiol