Orgyia postica

Posticlure [(6Z,9Z,llS,12S)-ll,12-epoxy-6,9-henicosadiene, 14] is the female sex pheromone of the tussock moth, Orgyia postica. Wakamura s first synthesis of 14 was achieved by employing Sharpless asymmetric epoxidation, and the final product was of 59% ee [38]. Mori prepared 14 of high purity as shown in Scheme 25 basing on asymmetric dihydroxylation (AD) [39]. Kumar also published an AD-based synthesis of 14 [40], which was more lengthy and less efficient than Mori s [39]. 

T., Yamazawa, H. and Ando, T. (2005). Sex pheromone and related compounds in the Ishigaki and Okinawa strains of the tussock moth Orgyia postica (Walker) (Lepidoptera Lymantriidae). Biosci. Biotechnol. Biochem., 69, 957-965. 

Wakamura, S., Arakaki, N., Yamamoto, M., Hiradate, S., Yasui, H., Yasuda, T. and Ando, T. (2001b). Posticlure a novel trans-epoxide as a sex pheromone component of the tussock moth, Orgyia postica (Walker). Tetrahedron Lett., 42, 687-689. 

Posticlure (pheromone of Orgyia postica) AI-2 (bacterial quorum-sensing signal)... 

In 2001 Wakamura et al. in Japan isolated, identified and synthesized (6Z,9Z,11S, 12S,)-11,12-epoxyhenicosadiene (94, Figure 4.45. trivial name posticlure) as the female sex pheromone of the tussock moth Orgyia postica, a pest on mango and litchi in Okinawa. Their synthesis relied upon Sharpless asymmetric epoxidation, and afforded 94 of 59% ee, which was purified by preparative HPLC on a chiral stationary phase to give pure 94. 

In another example, the organocatalytic a-chlorination was successfully employed to constmct the chiral epoxides in the synthesis of two insect sex pheromones 107 and 108, which were isolated from the pine looper moth Bupalus piniarins and the tussock moth Orgyia postica, respectively. The synthesis of these enantiopure compounds may offer a solution to pest control. 

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