Synthetic studies on bioactive natural products related to the chemical control of agricultural ecosystem

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Synthetic Studies were conducted on azadirachtin (1, insect antifeedant), (Z)-exo-α-bergamotenal (2, sex pheromone of Eysarcoris parvus), isorobinal (3, novel cyclic monoterpene from the astigmatid mite), volicitin (4, elicitor from the Spodoptera exigua), the sex pheromone of the citriculus mealybug (5), a phytoalexin isolated from Hyoscyamus albus (6), oryzalexin S (7, phytozlexin from the rice plant), tabtoxinine-β-lactam (8, phytotoxin from Pseudomonas tabaci), pyricuol (9, phytotoxin from Magnaporthe grisea), and ptericids A and B (10 and 11, auxin-like plant growth promoter from Streptomyces hygroscopicus). A model compound of 1 containg the bicyclo[2.2.1]heptane ring connected to the B ring was synthesized by using the Beckmann rearrangement of a petacyclic precursor. Synthesis of 2, 3, 4, 5, 9 was accomplished from farnesic acid, perilaldehyde, lactic acid, a-pinene, and 2,3-dimethylpheno1, respectively. Synthetic efforts toward 6, 7, 8, 10, and 11 were now in progress.