Beilstein J. Org. Chem.2021,17, 2716–2725, doi:10.3762/bjoc.17.183
, Härtelstr. 16–18, 04107 Leipzig, Germany 10.3762/bjoc.17.183 Abstract We present a systematic investigation on an improved variant of the N-acyl-Pictet–Spengler condensation for the synthesis of 1-benzyltetrahydroisoquinolines, based on our recently published synthesis of N-methylcoclaurine, exemplified by
(treatment with excess methyllithium) to give the corresponding alkaloids with free N–H function. This dual use of the ethoxycarbonyl group shortens the synthetic routes to hydroxylated 1-benzyltetrahydroisoquinolines significantly. Not surprisingly, these ten alkaloids did not show noteworthy effects on
relationships in this chemotype.
Keywords: acyl Pictet–Spengler reaction; alkaloids; antiproliferative activity; benzyltetrahydroisoquinolines; ion channels; protective group; total synthesis; Introduction
The benzylisoquinoline alkaloids are a large and diverse class of plant secondary metabolites including
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Graphical Abstract
Figure 1:
Prominent synthetic approaches to 1-benzyltetrahydroisoquinolines: Bischler–Napieralski, Pictet–Spe...