Issue 36, 2020

Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet–Spengler reactions

Abstract

Employing TBN/TEMPO as the catalysts and oxygen as the oxidant, the biologically and pharmaceutically significant tetrahydro-β-carboline and β-carboline alkaloid scaffolds that used to be obtained by multi-step processes can now be selectively obtained in only one-step via direct aerobic oxidative Pictet–Spengler reactions of tryptamines with alcohols under mild conditions, with water generated as the byproduct. In this reaction, TBN/TEMPO was interestingly found to be able to facilitate the cyclization step of the whole reaction. This method tolerates a variety of C- and N-substituted tryptamines, and both the more reactive benzylic and allylic alcohols and the less reactive aliphatic alcohols. This method can also be extended to dihydro-β-carboline synthesis and applied to the more available and more economical tryptophan for β-carboline synthesis, revealing its broad substrate scope and potential in synthetic applications.

Graphical abstract: Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet–Spengler reactions

Supplementary files

Article information

Article type
Communication
Submitted
28 Jul 2020
Accepted
21 Aug 2020
First published
27 Aug 2020

Org. Biomol. Chem., 2020,18, 7079-7085

Selective construction of alkaloid scaffolds by alcohol-based direct and mild aerobic oxidative Pictet–Spengler reactions

H. Liu, F. Han, H. Li, J. Liu and Q. Xu, Org. Biomol. Chem., 2020, 18, 7079 DOI: 10.1039/D0OB01549K

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