Satin moth

Leucomalure [15, a mixture of (3Zy6R y7S y9R ylOS ) and (3Z,6i, 7S, 9S, 10i )-ns-6,7-ds-9,10-diepoxy-3-henicosene] is the female sex pheromone of the Satin moth (Leucoma salicis) [41]. Its racemic and diastereomeric mixture... 

Male satin moths, Leucoma (Stilpnotia) salicis L. (Lepidoptera Lymantriidae), were attracted only to the 5Z, 6R, 7S, 9R, 105)-isomer out of the four (3Z )-cis-6,7-cis-9,10-diepoxy-3-henicosenes (leucomalure). This finding was confirmed by field tests conducted in Hungary, which... 

Satin moth, Leucoma salicis. All four isomers of (X )- i-cis-6,7-cis-9,10-diepoxyhenicose-nes were synthesized using D-xylose as the chirally pure starting material. 

PS-C (Am ano)-catalyzed asymmetric acetylation was a key step in the synthesis of all four stereoisomers of leucomalure 3Z)-cis,6,7-cis-9,10-diepoxy-3-henicosene], the female sex ph eromone of the satin moth Leucoma salicis.21 ... 

Muto, S. and Mori, K. (2003b). Synthesis of all four stereoisomers of leucomalure, components of the female sex pheromone of the satin moth, Leucoma salicis. Eur. 

A more convenient preparative method for D was devised later, as shown in Figure 4.30 [D in Figure 4.29 is (2R,3S)-A in Figure 4.30].58 Asymmetric acetylation of ( )-A with vinyl acetate in the presence of lipase PS-C gave acetate (2S,3R)-R (98.1% ee) and recovered alcohol (2R,3S)-A (99.5% ee) in almost quantitative yields after chromatographic separation. The building block (2R,3S)-A was successfully used for the synthesis of leucomalure [(3Z,6S,7/ ,9S,10/ )-86], the female sex pheromone of the Satin moth (Leucoma salicis).58,59... 

Z.6S,7R,9S,I0>- l.eucomalure tl ° FJ < HihitMf Satin moth (Leucoma sulids) Fs Stereoselective biocatalysis [172]... 

Asymmetric acetylation of ( )-epoxy alcohol 5 with vinyl acetate and lipase PS gave acetate (2S,3P)-21 and alcohol (2 R,3S)-5 (Figure 24.11) [5]. These products were obtained with satisfactory enantiomeric purities through a single enzymatic acet-ylahon. When t-butyldimethylsilyl protechve group was employed instead of the t-butyldiphenylsilyl group, the enantiomeric purity of the products was less satisfactory. The recovered alcohol (2P,3S)-5 was converted to leucomalure, the satin moth pheromone. 

Preparation of epoxide 2R,3S)-5, which was converted to ieuco-maiure (the pheromone of the satin moth). 

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