Journal Article

FZJ-2021-04338

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines

Klein, A. ; Albrecht, A. C.FZJ* ; Pietruszka, J. (Corresponding author)FZJ*

2021
MDPI Basel

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Please use a persistent id in citations: http://hdl.handle.net/2128/29781  doi:10.3390/catal11111389

Abstract: 1,2,3,4‑Tetrahydyroisoquinolines form a valuable scaffold for a variety of bioactive secondary metabolites and commercial pharmaceuticals. Due to the harsh or complex conditions of the conventional chemical synthesis of this molecular motif, alternative mild reaction pathways are in demand. Here we present an easy-to-operate chemoenzymatic one-pot process for the synthesis of tetrahydroisoquinolines starting from benzylic alcohols and an amino alcohol. We initially demonstrate the oxidation of 12 benzylic alcohols by a laccase/TEMPO system to the corresponding aldehydes, which are subsequently integrated in a phosphate salt mediated Pictet–Spengler reaction with m‑tyramine. The reaction conditions of both individual reactions were analyzed separately, adapted to each other, and a straightforward one-pot process was developed. This enables the production of 12 1,2,3,4‑tetrahydyroisoquinolines with yields of up to 87% with constant reaction conditions in phosphate buffer and common laboratory glass bottles without the supplementation of any additives.

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Contributing Institute(s):

1. Biotechnologie (IBG-1)
2. Institut für Bioorganische Chemie (HHUD) (IBOC)

Research Program(s):

1. 2171 - Biological and environmental resources for sustainable use (POF4-217) (POF4-217)

Appears in the scientific report 2021

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