(5R,7R)-5-Methylheptadecan-7-ol: a novel sex pheromone component produced by a female lichen moth, Miltochrista calamina, in the family Arctiidae

A methyl-branched heptadecanol was found in the pheromone gland extract of a female lichen moth, Miltochrista calamina (Arctiidae, Lithosiinae). GC-MS analyses of the alcohol and a hydrocarbon derived from it by subsequent treatments with methanesulfonyl chloride and LiAlD4 in microscale reactions indicated 5-methylheptadecan-7-ol (1) as one possible structure. The four stereoisomers of 1 in a ratio of 4:4:1:1 were prepared from (S)-beta-citronellol with 60% ee, and were separated by a combination of achiral and chiral HPLC columns. The absolute configuration of each isomer was determined by the comparison with the chromatographic behaviors of other samples synthesized by a different scheme, which applied the Jacobsen hydrolytic kinetic resolution of racemic 1,2-epoxydodecane to fix the configuration of the 7-hydroxy group. Only the (5R,7R)-isomer attracted male moths; thus, we concluded that M. calamina females secrete (5R,7R)-1 as a sex pheromone, indicating a new chemical class of lepidopteran female sex pheromones. (C) 2011 Elsevier Ltd. All rights reserved,