One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction

An efficient and convenient strategy has been successfully developed for the preparation of novel hydroxylated alkaloid derivatives (also called fused multicyclic iminosugars) from <i>p</i>-toluenesulfonylated sugars through a Pictet-Spengler-type mechanism. This method is highly stereoselective, does not require metal catalysts, and capable of conducting gram level reactions (with a 53% yield). Some of such iminosugars had an intermediate antiproliferative effect on HCT116 tumor cells.

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Publication Details

Journal
Molecules
Published
2024-12-03
DOI
https://doi.org/10.3390/molecules29235709
Citations
2
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.50

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article

One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction

Chen Hua, Jilai Wu, Likai Zhou, Feng Liu et al.
2 citations
Molecules
Carbohydrate Chemistry and Synthesis
0.50
article

One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction

Chen Hua, Jilai Wu, Likai Zhou, Feng Liu, Song Xie, Na Ma, Weilin Yang, Lili Wang
article en
2 citations

Abstract

An efficient and convenient strategy has been successfully developed for the preparation of novel hydroxylated alkaloid derivatives (also called fused multicyclic iminosugars) from <i>p</i>-toluenesulfonylated sugars through a Pictet-Spengler-type mechanism. This method is highly stereoselective, does not require metal catalysts, and capable of conducting gram level reactions (with a 53% yield). Some of such iminosugars had an intermediate antiproliferative effect on HCT116 tumor cells.

MoleculesVol. 29(23)
Hebei University (CN), Xingtai University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Hebei Province, Hebei University
Openalex Percentile: Top 37%
Carbohydrate Chemistry and Synthesis
0.50
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One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction — Chen Hua, Jilai Wu, et al. · Molecules (2024) | TGRS Research Map | TGRS