立体中心
化学
立体化学
全合成
天然产物
重排
四级碳
庚烷
双环分子
裸鳃类
组合化学
对映选择合成
有机化学
催化作用
古生物学
软体动物
生物
作者
Alina Eggert,Karl T. Schuppe,Hazel Leanne Sarah Fuchs,Mark Brönstrup,Markus Kalesse
标识
DOI:10.1021/acs.orglett.3c03717
摘要
We present the second total synthesis of (±)-acanthodoral, a sesquiterpenoid derived from the marine nudibranch Acanthodoris nanaimoensis. Our approach involves a concise three-step transformation from a previously reported compound, resulting in the formation of a less strained precursor of the bicyclo[3.1.1]heptane core and both all-carbon quaternary stereocenters characteristic of the natural product. Notably, this synthetic route incorporates two pivotal steps: a Sm(II)-induced 1,2-rearrangement and a semipinacol rearrangement.
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