Synthesis and field evaluation of the sex pheromone analogues to soybean pod borer Leguminivora glycinivorella.

In order to develop efficient lures for soybean pod borer Leguminivora glycinivorella (Matsumura) in China, (E,E)-8,10-dodecadienyl acetate (EE-8,10-12:Ac), the main component of the pheromone of L. glycinivorella, and 12 structurally-related compounds were synthesised in good overall yields, regiospecificities, and stereo-selectivities via coupling reactions catalysed by Li2CuCl4. The effect of different synthetic compounds, alone or in combination with EE-8,10-12:Ac, on numbers of captured L. glycinivorella males was evaluated. EE-8,10-12:Ac, (E)-10-dodecenyl acetate (E-10-12:Ac), (E)-8-dodecenol (E-8-12:OH), tetradecyl acetate (14:Ac), and (Z)-9-tetradecenyl acetate (Z-9-14:Ac) alone displayed different attractiveness to L. glycinivorella males. 14:Ac, E-8-12:OH, E-10-12:Ac, (E,E)-8,10-dodecadienal (EE-8,10-12:Ald), (E)-8-dodecenal (E-8-12:Ald), (E)-10-dodecenal (E-10-12:Ald) and Z-9-14:Ac all showed a synergistic effect to EE-8,10-12:Ac at certain dosages. The binary mixtures of EE-8,10-12:Ac and E-10-12:Ald, Z-9-14:Ac,14:Ac, E-8-12:Ald, EE-8,10-12:Ald, E-8-12:OH, or E-10-12:Ac in suitable ratios give 17.00-, 10.98-, 10.67-, 6.73-, 5.54-, 4.30- and 4.50-fold increases in trap catch, respectively, over the standard pheromone lure, and as novel pheromone blends, demonstrated potential use in pheromone traps to monitor or control L. glycinivorella populations in China.

Novel 5, 6-Dihydropyrrolo[2,1-a]isoquinolines as Scaffolds for Synthesis of Lamellarin Analogues.

AS CORE SKELETONS OF LAMELLARINS: 5,6-Dihydropyrrolo[2,1-a]isoquinolines are one of the important alkaloids that exhibit significant biological activities, in this study, an efficient synthetic route was described for two novel compounds, 5,6-dihydropyrrolo[2,1-a]isoquinolines I and II. Compound I was synthesized from isovanillin with 28.3% overall yield by a six-step reaction while II from 2-(3, 4-dimethoxyphenyl) ethanamine was with 61.6% overall yield by a three-step reaction. And the structures of these two compounds were confirmed by means of IR spectrum, (1)H NMR, (13)C NMR, MS, HRMS, and melting point measurements.

Synthesis of a new intermediate for bioactive Lamellarins.

This paper reports two methods of synthesis for 1,2,4-trimethoxy-5-(1-methyl-2-phenyl-vinyl)-benzene, which was a key intermediate to synthesize the various Lamellarins. One method is by using the Wittig-Horner reaction and another is by the Grignard reaction. By conducting contrast experiments, we got the optimal reaction parameters for high yields. The newly formed intermediate was identified by means of IR spectrum, (1)H-NMR, (13)C-NMR and melting point measurements.