Short Synthesis of the Monoterpene Indole Alkaloid (+/-)-Arbornamine
Short Synthesis of the Monoterpene Indole Alkaloid (+/-)-Arbornamine
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单萜吲哚生物碱 (i-)-Arbornamine 的简短合成
DOI：
10.1021/acs.joc.8b00529
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发表时间：
2018
影响因子：
3.6
通讯作者：
Yang Yu-Rong
中科院分区：
文献类型：
--
作者：
Zheng Yu;Yue Bei-Bei;Wei Kun;Yang Yu-Rong
首次完成了单萜吲哚生物碱（±）-arbornamine（1）的全合成，从三个易得的已知化合物出发，仅经6步反应，总收率31%。该合成的特征在于涉及Pictet-Spengler环化/分子内氨解的级联反应，以在单一化学操作中产生arbornamine（1）的四环核心。随后的5成1的阐述是由一个关键的还原赫克反应和全球减少。
The first total synthesis of the monoterpene indole alkaloid (±)-arbornamine (1) has been completed, which proceeds in only 6 steps and 31% overall yield from three readily available, known compounds. The synthesis features a cascade involving a Pictet–Spengler cyclization/intramolecular ammonolysis to create the tetracyclic core of arbornamine (1) in a single chemical operation. The subsequent elaboration of5into1was effected by a key reductive Heck reaction and global reduction.