Sex Pheromone Of Cigarette Beetle Research Articles

Synthesis of a biologically active analog of the sex pheromone of cigarette beetle (Lasioderma serricorne)

A simple synthesis of a diastereomeric mixture of 7-hydroxy-4,6-dimethylnonan-3-ones was carried out. In the biological action, it is an analog of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne).

Enantioselective synthesis of (−)-serricornin, a sex pheromone of a female cigarette beetle ( Lasioderma serricorne F.)

(−)-Serricornin, a sex pheromone of a cigarette beetle ( Lasioderma serricorne F.), has been synthesized highly stereoselectively starting from ( Z)-4-benzyloxy-2-buten-1-ol by employing the Katsuki-Sharpless asymmetric epoxidation and two stereospecific methylation reactions, the regioselective γ-methylation of a γ,δ-epoxy acrylate by trimethylaluminum and α-methylation of a δ-lactone, as key steps.

Conformational analysis of serricornin: Application of molecular mechanics calculations to stereochemical assignment of serricornin, sex pheromone of cigarette beetle (Lasioderma serricorne F.)

Conformational analysis using molecular mechanics (MM) was performed for a determination of the stereochemistry of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne F.). An exhaustive conformational analysis using MM2 calculations with algorithms for covering torsional energy surfaces of flexible molecules furnishes coordinates and steric energies of all local energy minimum conformers of serricornin, both acyclic and the corresponding cyclic forms. These coordinates gave angles required for the calculation of vicinal H/H coupling constants ((3) J HHs) of each energy minima by Altona's modified Karplus equation. The Boltzmann distributions of all local energy minima were calculated from their steric energies to furnish populations of each energy minimum conformer. Populationweighted averaged(3) J HHs of four enantiomeric pairs, (S (*),S (*),S (*))-, (S (*),S (*),R (*))-, (S (*),R (*),S (*))-, and (R (*),S (*),S (*))-serricornins were calculated from the data above. The observed(3) J HHs of the naturally occurring serricornin, both acyclic and cyclic forms, are fitted best to calcd.(3) J HHs of (4S (*), 6S (*), 7S (*))-acyclic and (3S (*), 5S (*), 6S (*))-cyclic serricornin, respectively, among those of four enantiomeric pairs of serricornin.

Absolute stereochemistry of serricornin, the sex pheromone of cigarette beetle, as determined by the synthesis of its (4S,6R,7R)-isomer

The absolute stereochemistry of serricornin was determined to be (4S,6S,7S) by the synthesis of its (4S,6R,7R)-isomer using a carbohydrate synthon.

Pheromone synthesis. Stereoselective synthesis of erythro-serricornin,(4R,6R,7S)-,and (4S,6R,7S)-4,6-dimethyl-7-hydroxynonan-3-one,stereoisomers of the sex pheromone of cigarette beetle.

A stereoselective synthesis of erythro-serricornin [(4RS, 6R, 7S)-4, 6-dimethyl-7-hydroxynonan-3-one] was completed starting from L-(+)-tartaric acid. The relative configuration of C(6)-methyl and C(7)-hydroxyl groups in naturally occurring serricornin was threo.

微量生理活性物質とその利用 たばこの香気と性フェロモン

The present article involves the studies on aroma constituents of turkish tobacco and the sex pheromone of cigarette beetle, of which the former is considered to be the biologically active substances to human and the both are to the insect.A comprehensive investigation of aroma constituents of Turkish tobacco showed the existence of terpenoid acids related to tobacco thunberganoids. The degradation of thunberganoids to these terpenoid acids are considered to be closely related to the formation of the tobacco characteristic aroma.In the course of our another studies on the biologically active substances to cigarette beetle, a serious pest of cured tobacco leaves, a sex pheromone, 4, 6-dimethyl-7-hydroxynonan-3-one (serricornin) and other 4, 6-dimethylnonane derivatives as minor components were isolated. The presence of these 4, 6-dimethylnonane derivatives suggests that these pheromone components are derived from the polyketide biosynthesis.These biologically active substances were synthesized in practical scale and now the applications of these chemicals as tobacco flavors and the attractants of cigarette beetle are in progress.

A novel synthesis of (.+-.)-serricornin 4,6-dimethyl-7-hydroxy-nonan-3-one the sex pheromone of cigarette beetle (Lasioderma serricorne F.)

A novel synthesis of (.+-.)-serricornin 4,6-dimethyl-7-hydroxy-nonan-3-one the sex pheromone of cigarette beetle (Lasioderma serricorne F.)

Synthesis of (±)-Serricornin, 4, 6-Dimethyl-7-hydroxy-nonan-3-one, A Sex Pheromone of Cigarette Beetle (Lasioderma serricorne F.)

Synthesis of (±)-Serricornin, 4, 6-Dimethyl-7-hydroxy-nonan-3-one, A Sex Pheromone of Cigarette Beetle (Lasioderma serricorne F.)