4 馬鈴薯夏疫病菌代謝植物毒素の構造と合成

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Alternaria solani, causal organism of early blight disease on potato produces several metabolites whose structures have been clarified. Recently presence of two other host specific toxin in the culture filtrate of the fungus has been reported. From the filtrate four new phytotoxic compounds, solanapyrones A(1), B(2), C(3) and zinnolide(4) have been isolated. These structures have been elucidated on the basis of spectroscopic data and chemical reaction. The structure of 2 was confirmed by correlation with 1. Further, zinnolide(4) was converted to a known phthalide 9 to prove the structure. Absolute configuration of solanapyrone A(1) was determined by the application of CD exiton chirality method to the dibenzoate derivative 13. In order to confirm the structure and to develop an effective synthetic method, synthesis of solanapyrone A(1) has been completed as follows. The pyrone moiety, the thioacetal 16, was prepared from dehydroacetic acid through 5 steps, and the diene moiety, the aldehyde 19, was derived from sorbic acid. Aldol condensation of 16 with 19 and dehydration of the product afforded the triene 20, which was subjected to intramolecular Diels-Alder reaction heating at 170-190℃ to yield a mixture of two products. The mixture was treated with thallium nitrate to give (±)-solanapyrone A(1), and the diastereoisomer 21 in a ratio of 2:3. The spectroscopic data of (±)-1 are completely identical with those of natural sample.
天然有機化合物討論会の論文
1986-09-09

4 馬鈴薯夏疫病菌代謝植物毒素の構造と合成

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