The effect of carbonyl on the isomerization of a galanthan ring system and total synthesis of (+/-)-beta-lycorane
The effect of carbonyl on the isomerization of a galanthan ring system and total synthesis of (+/-)-beta-lycorane
复制标题
羰基对加兰坦环体系异构化及(i-)-β-lycorane全合成的影响
DOI：
10.1039/d0ob02398a
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发表时间：
2021
影响因子：
3.2
通讯作者：
an
中科院分区：
文献类型：
--
作者：
Liang Leilei;Li Ji;Shen Baochun;Zhang Yili;Liu Jianping;Chen Jingbo;Liu D;an
石蒜碱类生物碱因其独特的生物活性而成为药物开发的优先结构。本文证明了C环上的羰基在合成过程中对立体选择性起着关键作用，具有顺式-B/C环的加兰他敏骨架在其存在下更稳定。此外，通过Michael加成反应构建了一个含trans-B/C环的加兰他敏骨架，成功地完成了（±）-β-石蒜烷的全合成。该系统可应用于具有类似立体化学设置的其他结构类型。
Lycorine-type alkaloids are privileged structures in drug development due to their attractive biological activities. In this paper, the carbonyl on the C ring was proved to have played a critical role in stereoselectivity during the synthesis process, and the galanthan skeleton with a cis-B/C ring is more thermodynamically stable in its presence. Furthermore, the total synthesis of (±)-β-lycorane was successfully completed by employing the Michael addition reaction to construct the galanthan skeleton with a trans-B/C ring. This system might be applied to other structural types with similar stereochemistry setting.