65(PA2-5) 分子内Diels-Alder反応による(-)-ベーテノンC、(+)-ディプロディアトキシンの合成研究(ポスター発表の部)

概要

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Betaenone C(1) is one of Phytotoxins isolated from culture filtrate of Phoma betae Fr., causal fungus of leaf spot disease of sugar beat. It exhibited the highest phytotoxic activity among betaenones to cause wilting of the host plant. Our synthetic strategy of 1 involves the intramolecular Diels-Alder reaction of chiral trienone 4, which would be a key intermediate leading to betaenones in the biosynthesis. The trienone is retrosynthesized into three segments A, B and C. Segment B derived from a known 9 which was obtained by Sharpless epoxidation of nerol was condensed with segments (±)-A and C following the Kocienski-Lythgoe-Julia method and then Wittig-Horner reaction in order. The intramolecular Diels-Alder reaction of 4 is now in progress. (+)-Diplodiatoxin (2) is a mycotoxin isolated from maize infected with Diplodia maydis. In the 27th symposium we already reported the total synthesis of 2 following the same strategy as that of betaenone C. We wish to report here newly developed synthetic methods of segment B in order to provide sufficient amount of 2 for study of structure-activity relationship.
天然有機化合物討論会の論文
1987-07-25