化学
全合成
羟醛反应
级联
立体专一性
立体化学
天然产物
复分解
级联反应
戒指(化学)
烯烃纤维
组合化学
有机化学
催化作用
聚合物
色谱法
聚合
作者
Moritz J. Classen,Bilal Kicin,Vincent A. P. Ruf,Alexander Hamminger,Loélie Ribadeau-Dumas,Willi Amberg,Erick M. Carreira
摘要
A total synthesis of the ingenane-derived diterpenoid (+)-euphorikanin A is described. Key to the strategy is a stereocontrolled one-pot sequence consisting of transannular aldol addition reaction, hemiketal formation, and subsequent semipinacol rearrangement that efficiently leads to the complete euphorikanin skeleton. Atroposelective ring-closing olefin metathesis proved critical for the stereospecific cascade, leading to formation of a (Z)-bicyclo[7.4.1]tetradecenone core. An additional salient feature of the route is pyrolysis of a bis-methylxanthate to cleanly furnish the natural product.
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