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A modular approach to the bisbenzylisoquinoline alkaloids tetrandrine and isotetrandrine

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Abstract

An efficient racemic total synthesis of the bisbenzylisoquinoline alkaloids tetrandrine and isotetrandrine in four different routes is reported herein. Key steps of the synthesis include N-acyl Pictet–Spengler condensations to access the tetrahydroisoquinoline moieties, as well as copper-catalyzed Ullmann couplings for diaryl ether formation. Starting from commercially available building blocks tetrandrine and isotetrandrine are accessed in 12 steps. Depending on the sequence of the four central condensation steps, equimolar mixtures of both diastereomers or predominantly tetrandrine or its diastereomer isotetrandrine are obtained. Through computational analysis we were able to rationalize the differences in the observed diastereomeric specificities.

Graphical abstract: A modular approach to the bisbenzylisoquinoline alkaloids tetrandrine and isotetrandrine

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Supplementary files

Article information


Submitted
14 Jan 2020
Accepted
13 Feb 2020
First published
19 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

A modular approach to the bisbenzylisoquinoline alkaloids tetrandrine and isotetrandrine

R. Schütz, M. Meixner, I. Antes and F. Bracher, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00078G

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