Ruby tiger moth

Z,9S,10 )-9,10-Epoxyhenicos-6-ene (13) is the female sex pheromone of moths such as ruby tiger moth (Phragmatobiafuliginosa), fruit-piercing moth (Oraesia excavata), and painted apple moth (Teia anartoides). Scheme 23 summarizes Shi s synthesis of 13 based on Sharpless asymmetric dihydroxylation (AD) [36]. Mori synthesized 13 employing lipase to prepare A (Scheme 24) [37]. Alkylation of the acetylide anion C was possible neither with tosylate nor with iodide, but triflate B could alkylate C to give D. 

Brevet, J.-L. and Mori, K. (1992). Pheromone synthesis CXXXIX. Enzymatic preparation of (2S,3R )-4-acetoxy-2,3-epoxybutan- l -ol and its conversion to the epoxy pheromones of the gypsy moth and the ruby tiger moth. Synthesis, 1992, 1007-1012. 

A number of papers deal with chiral synthesis of epoxides. The pheromone of the ruby tiger moth (58) has been prepared in 10... 

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