title: Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal.
abstract: The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three well-established procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.
authors.affiliation: Photosensitive Materials Research Center, Toyo Gosei Co., Ltd., Wakahagi, Chiba, Japan.
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Shikichi
authors.forename: Kenji
authors.initials: K
authors.lastname: Mori
mesh_terms: D000080462:Acyclic Monoterpenes; D000447:Aldehydes / Q000737:chemistry*; D000818:Animals; D060326:Chemistry Techniques, Synthetic; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D039821:Monoterpenes / Q000737:chemistry*; D009036:Moths / Q000737:chemistry*; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C526402:14-methyl-2-octadecanone; C526403:6,14-dimethyl-2-octadecanone; C526401:6-methyl-2-octadecanone; D000080462:Acyclic Monoterpenes; D000447:Aldehydes; D007659:Ketones; D039821:Monoterpenes; D012724:Sex Attractants; C108217:citronellal