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

Likai Zhou, Na Ma, Jilai Wu, Weilin Yang, Lijing Feng, Song Xie, Lili Wang, Hua Chen, Francisco Leon · 2024

Read One-Pot Synthesis of Hydroxylated Alkaloids from Sugars via a Pictet–Spengler-Type Reaction by Likai Zhou, Na Ma, Jilai Wu, Weilin Yang, Lijing Feng, Song Xie, Lili Wang, Hua Chen, Francisco Leon (2024) in the Tower of Babel, a free online library of public-domain works preserved in clean, searchable text. No sign-up. The full text is served as a plain-text file at a predictable URL, where text is present: https://antarctic-labs.com/tower-of-babel/pmc-11643748.txt.

Description

Likai Zhou and co-authors cook up new sugar based alkaloids in one pot in this 2024 paper. Their targets are hydroxylated alkaloids, also seen as fused ring iminosugars, ring shaped sugar mimics that can block enzymes and interest drug hunters.

The route starts from sugars fitted with a tosyl group and runs through a Pictet-Spengler type reaction, a classic ring closing step. The method picks one spatial arrangement of the product with high selectivity, needs no metal catalyst, and scales to gram amounts, giving a fifty-three percent yield in the large run. Some of the new iminosugars showed a middling power to slow the growth of HCT116 tumor cells in tests.

Catalog record

CREATORLikai Zhou, Na Ma, Jilai Wu, Weilin Yang, Lijing Feng, Song Xie, Lili Wang, Hua Chen, Francisco Leon
YEAR2024
COLLECTIONPAPERS
FORMATTXT
FILE SIZE17 KB
VERSION1.0
LICENSECC BY 4.0
RIGHTSCC BY
SOURCEEurope PMC

Source: https://europepmc.org/articles/PMC11643748

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