Synthesis and absolute configuration of the male aggregation pheromone of the stink bug Erysarcoris lewisi (Distant), (2Z,6R,1′S,5′S)-2-methyl-6-(4′-methylenebicyclo[3.1.0]hexyl)hept-2-en-1-ol

Stereochemical studies on pheromonal communications

“…In 2007 to 2008, synthesis of 9 and its isomers was executed by us in two different ways employing either chemical or enzymatic asymmetric reactions. 23 , 24 ) Figure 5 summarizes the chemical asymmetric synthesis of (2 Z ,6 R ,1′ S ,5′ S )- 9 . 24 ) The natural isomer (2 Z ,6 R ,1′ S ,5′ S )-(+)- 9 was of course as bioactive as the natural product, while (2 Z ,6 S )-isomers and (2 Z ,6 R ,1′ R ,5′ R )-(−)- 9 were inactive.…”

“… 23 , 24 ) Figure 5 summarizes the chemical asymmetric synthesis of (2 Z ,6 R ,1′ S ,5′ S )- 9 . 24 ) The natural isomer (2 Z ,6 R ,1′ S ,5′ S )-(+)- 9 was of course as bioactive as the natural product, while (2 Z ,6 S )-isomers and (2 Z ,6 R ,1′ R ,5′ R )-(−)- 9 were inactive. No antagonistic activity was observed with the (2 Z ,6 S )-isomers.…”

Pheromones in Chemical Communication

“…15 For this purpose, the diastereomeric mixture of ketone (6R)-16 (Scheme 5.3) was reduced with L-Selectride to give a mixture ), CH 2 Cl 2 , room temperature, (95% quant. ); (d) K 2 CO 3 , MeOH (quant.…”

“…The lower half of Scheme 5.3 summarizes our recent synthesis of the pheromone. 15 Hodgson's intramolecular cyclopropanation procedure (20 ! 21) could be employed successfully.…”

Lipases and Esterases as User‐Friendly Biocatalysts in Natural Product Synthesis

“…Treatment of the mixture with vinyl acetate and lipase PS-D in Et 2 O was followed by SiO 2 chromatography to give acetate (6R,1′R,4′R,5′S)-52 and recovered (6R,1′S,4′S,5′R)-51. The latter was converted to the pheromone of the stink bug, Eysarcoris lewisi(Figure 24.26)[30].…”