89 シトレオビリジノール及び関連代謝産物の構造及び合成

概要

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Citreoviridin, a toxic yellow metabolite of Penicillium citreoviride B. has been well-known. In connection with our investigation directed toward isolations and syntheses of metabolites of P. citreoviride B. (IFO 6050 and 6200), the following subjects would be discussed. 1. Citreoviridin (1) and (+)-citreoviral (2) were synthesized from D-glucose. The absolute structures of 1 and 2 could be established by this synthetic study. (±)-Citreoviral (2) was also synthesized by two different routes. It was found out that the intermediate (8) was the suitable compound for synthesis of 2,6-dioxabicyclo[3. 2. 1]octan derivative. 2. The absolute structures of 11 and newly isolated 12 were chemically confirmed. The stereostructures of the bicyclo derivatives were elucidated on the basis of molecular mechanics calculation. 3. The isolations and structures of 20, 21, 22 and 23 were established. Biogenetically, 20 and 21 have the same intermediate as 11 and 12. On the other hand, 22 and 23 were the new phenolic metabolites of P. citreo-viride B. (IFO 4692).
天然有機化合物討論会の論文
1985-09-07