Four-step continuous-flow total synthesis of (−)-debromoflustramine B using a chiral heterogeneous Pd NP catalyst

Abstract

Various prenylated indoline alkaloids with diverse biological activities, including (−)-debromoflustramine B with significant butyrylcholinesterase inhibitory activity, could be synthesized by dearomative prenylation reactions of tryptophan derivatives. However, previously reported dearomative prenylations were limited to batch reactions at the milligram scale, requiring multistep reactions and complex post-processing to obtain the desired natural products. The more efficient synthesis of alkaloids remains challenging, as does the recovery of expensive catalysts. Herein, we developed a chiral heterogeneous Pd nanoparticle (NP) catalyst supported on a polymer, which produces indoline alkaloids in high yields with excellent enantioselectivities. Additionally, the first gram-scale four-step continuous-flow total synthesis of (−)-debromoflustramine B was successfully achieved with this chiral Pd heterogeneous catalyst, requiring only a simple post-processing step.

Graphical abstract: Four-step continuous-flow total synthesis of (−)-debromoflustramine B using a chiral heterogeneous Pd NP catalyst

Supplementary files

Article information

Article type
Edge Article
Submitted
28 May 2024
Accepted
07 Sep 2024
First published
09 Sep 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024, Advance Article

Four-step continuous-flow total synthesis of (−)-debromoflustramine B using a chiral heterogeneous Pd NP catalyst

J. Wang, F. Liang, Z. Dong, J. Huang, Y. Zhu, H. You and F. Chen, Chem. Sci., 2024, Advance Article , DOI: 10.1039/D4SC03471F

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