对映体药物
化学
全合成
氢胺化
对映体
生物碱
产量(工程)
立体化学
试剂
组合化学
对映选择合成
有机化学
催化作用
分子内力
冶金
材料科学
作者
Mátyás Milen,Tímea Szabó,Funda Lidya Görür,Simon Horváth,Balázs Volk
出处
期刊:Synthesis
[Georg Thieme Verlag KG]
日期:2022-02-15
卷期号:54 (17): 3867-3873
被引量:2
标识
DOI:10.1055/s-0041-1737830
摘要
Abstract A new total synthesis of the pharmacologically active β-carboline alkaloid brevicolline is described. The new synthetic approach is based on a commercially available and inexpensive starting material and reagents leading to a practical synthesis of the racemic target molecule, the natural (S)-enantiomer, and its antipode. Initially, the construction of the β-carboline skeleton and functionalization at the C(4) position have been accomplished. The formation of dihydropyrrole structural unit was obtained as the result of an Au-catalyzed hydroamination reaction, which was followed by a reduction that led to the chiral intermediate. The synthetic route described here is developed to ensure the sustainable access of the racemic brevicolline in 11 steps with improved 48% overall yield compared to the previously reported methods.
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