作者:Masaya Ichikawa、Masaki Takahashi、Sakae Aoyagi、Chihiro Kibayashi
DOI:10.1021/ja0401702
日期:2004.12.1
The first total syntheses of new monoterpene alkaloids (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine, corresponding to the natural enantiomers, have been accomplished. The strategy for the synthesis of these natural products utilized 6-epi-incarvilline as a common precursor, which was assembled by a three-component coupling reaction using (4S)-4-siloxy-2-cyclopenten-1-one to construct
与天然对映体相对应的新单萜生物碱 (-)-incarvilline、(+)-incarvine C 和 (-)-incarvillateine 的首次全合成已经完成。这些天然产物的合成策略利用 6-epi-incarvilline 作为常见的前体,通过三组分偶联反应使用 (4S)-4-siloxy-2-cyclopenten-1-one 组装以构建适当的三取代的环戊酮,然后通过还原性 Heck 型反应闭环到顺式-全氢-2-吡啶骨架。此外,还研究了固态肉桂酸衍生物的拓扑化学控制 [2 + 2] 光二聚化,用于立体定向构建 1,2,3,4-四取代环丁烷环,作为获取 (-)-incarvillateine 的一种手段。