7環性アコニットアルカロイド(±)-Nominineの全合成
書誌事項
- タイトル別名
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- Total Synthesis of (±)-Nominine, a Heptacyclic Hetisine-Type Aconite Alkaloid
抄録
The palladium-catalyzed intramolecular α-arylation of formyl group was successfully applied to a total synthesis of (±)-nominine, a heptacyclic hetisine-type aconite alkaloid isolated from Aconitum sanyoense Nakai in 1956. The synthesis consists of forty-steps from 2-bromo-5-methoxyphenethyl iodide, and constitutes the first total synthesis of a hetisine-type aconite alkaloid, the sole representative aconite skeleton whose total synthesis has remained unsuccessful. Key steps other than the above α-arylation are (i) acetal ene-reaction to form the C14–C20 bond, (ii) LiAlH4 reduction of cyano-enol silyl ether to form the N–C6 bond, (iii) radical cyclization from enyne precursor to construct the methylenebicyclo[2.2.2]octane framework, and (iv) allylic oxidation with SeO2–tert-BuOOH to introduce 15β-OH. Completion of the synthesis was verified unequivocally by single crystal X-ray analysis of (±)-nominine.
収録刊行物
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- 反応と合成の進歩シンポジウム 発表要旨概要
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反応と合成の進歩シンポジウム 発表要旨概要 30 (0), 288-289, 2004
日本薬学会化学系薬学部会
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- CRID
- 1390001205634987648
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- NII論文ID
- 130006997461
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- データソース種別
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- JaLC
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