60(P30) 間接電解酸化をキーステップとするユーグロバールの合成(ポスター発表の部)
スポンサーリンク
概要
- 論文の詳細を見る
Natural euglobals and their skeletones were synthesized by electrochemical method. Euglobals were isolated from Eucalyptus spp. as inhibitors of the Epstein-Barr virus activation, or as antimalarial compounds. These compounds have unique chroman or spirochroman skeletons. We envisioned that the synthesis of natural euglobals could be readily accessible by the cycloaddition of terpenes and quinone methides which has been regarded as a biogenetic pathway. Presently, two electrochemical methods were introduced to accomplish the generation of quinone methides and their interemolecular cycloaddition with terpenes which has been proven difficult. Firstly, euglobal G1, G2, G3, T1 and IIc were synthesized by the electrochemical oxidation of grandinol using DDQ as a redox mediator on a PTFE (poly-tetrafluoroethylene) fiber coated Pt electrode. In this electrochemical system, hetero Diels-Alder reaction of quinone methides and terpenes was successively promoted, and DDQ was effectively regenerated. Spectral data of synthesized euglobals were completely identical with those of natural products, and their absolute configurations were also elucidated. Secondly, o-quione methides were generated by the electrochemical oxidation of 2-[1-(phenylsulfanyl)alkyl]phenols to give corresponding cycloadducts with terpenes. In this system, cat. amount of methylene blue was introduced as a mediator of photo-electrochemical oxidation of sulfides. Important syntetic intermediates for e.g. euglobal 1a_1 and 1a_2were synthesized to give o-quinone methide under lower potential condition.
- 天然有機化合物討論会の論文
- 1997-07-20
著者
関連論文
- 60(P30) 間接電解酸化をキーステップとするユーグロバールの合成(ポスター発表の部)
- キツネノマゴ(Justicia procundens)に含まれるアリールナフタリドリダナンの抗ウイルス活性 : 有機化学・天然物化学
- ユーグロバールの合成 : 有機化学・天然物化学
- 水相における電解酸化によるキノンの生成とそのDiels-Alder反応 : 有機化学・天然物化学
- フッ素樹脂を利用した電極反応によるキノン類の生成とそのDiels-Alder反応 : 有機化学,天然物化学
- 電解酸化によるeuglobal基本骨格の合成 : 有機化学,天然物化学
- 抗アレルギー・抗ウィルス活性を示すAcylphloroglucinol誘導体とアミンとの反応 : 有機化学・天然物化学
- Synthesis of Patulin and Its Cyclohexane Analogue from Furan Derivatives
- リン脂質による乳化状態の核磁気共鳴による解析(第2報)(食品-物性, 物理化学, 分析-)
- リン脂質による乳化とその乳化状態の31P-NMRによる解析
- 96(P-53) 3-イソシアノテオネリンの短工程合成およびその類似体の付着阻害活性(ポスター発表の部)
- 電解酸化系における疎水性反応場を用いた付加環化反応
- 抗ウイルス活性を示すフロログルシノール誘導体
- リン脂質による乳化とその乳化状態の31P-NMRによる解析