先導的バイオサイエンスのための有機合成化学的展開 : 生体内Diels-Alder反応の可能性

概要

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A number of bioactive compounds, which are presumably biosynthesized through Diels-Alder reaction in plants and microorganisms, have been found. However, no direct evidences for the reaction was obtained. Biosynthetic studies have been performed to prove the hypothesis with a few phytotoxins. Feeding experiments of solanapyrone A with labelled precursors, and the isolation and the synthesis of the diastereomer, solanapyrone D, strongly suggest the participation of biological Diels-Alder reaction. The treatment of <I>P</I>. betae with cytochrome P-450 inhibitors accumulated an intermediate, probetaenone I, which structure was confirmed by the synthesis. The same treatment of C, <I>subaffine</I> accumulated prochaetoglobosins. These are also evidences for biological Diels-Alder reaction. Chemical synthesis of diplodiatoxin and betaenone C have made possible to provide key intermediates for incorporation study of biological Diels-Alder reaction.
社団法人有機合成化学協会の論文