Synthetic Studies on Semiochemicals for the Control of Agricultural Pests

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The total synthesis of the following biologically active natural products have been accomplished : (1)enokipodins A,B,C, and D (highly oxygenated a-cuparenone-type sesquiterpenoids exhibiting antimicrobial activity produced by the edible mushroom, Flammulina velutipes) ; (2)pteridic acids A and B (potent plant-growth promoters possessing unique spirocyclic polyketidic structures isolated form the phytoepiphytic actinomycete, Streptomyces hygroscopicus TP-A0451) ; (3)tabtoxinine-β-lactom (a phytotoxin produced by the pathogen Pseudomonas syringae pv. tabaci) ; (4)pteroenone (a defensive metabolite of the pteropod, Clione antarctica) ; (5)the major sex pheromone components of the fruit flies, Drosophila ananassae and D.pallidosa ; (6)communiols A,B,C,D,E,F,and H (antimicrobial metabolites produced by the coprophilous fungus, Podospora communis) ; (7)pyricuol (a phytotoxin produced by the rice blast fungus, Magnaporthe grisea) ; (8)gizzerosine (a potent inducer of gizzard erosion in chicks contained in heat-treated fish meal) ; (9)apoptosis-inducing polyunsaturated conjugated fatty acids ; (10)litseaverticillols A and B (anti-HIV sesquterpenoids bearing a novel carbon sketeton produced by the perennial shrub, Litsea verticillata). Partial syntheses of pamamycin-635A (an arerial mycelium-inducing metabolite produced by Streptomyces alboniger) and elaiophylin (an antibiotic as well as a plant-growth inhibitor) were conducted. Studies directed toward the total synthesis of azadirachtin (a potent antifeedant contained in the neem tree, Azadirachta indica) was also made.