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Synthesis of 14‐[ 2 H]arteether, an experimental antmalarial drug
Author(s) -
Hu Yulin,
Ziffer Herman
Publication year - 1991
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580291205
Subject(s) - chemistry , yield (engineering) , alcohol , deuterium , stereochemistry , chemical synthesis , catalysis , sequence (biology) , medicinal chemistry , organic chemistry , in vitro , biochemistry , materials science , physics , quantum mechanics , metallurgy
A reaction sequence employing a fungus mediated oxidation of arteether, an experimental antimalarial drug, was used to introduce a hydroxyl group on C‐14. The hydroxyl group was replaced by a deuterium by preparing the tosylate and reductively cleaving it with sodium borodeuteride in DMSO. A reaction sequence to introduce a second label was also demonstrated it involved oxidation of the alcohol, with catalytic quantities of tetra‐n‐propylammonium perruthenate, followed by reduction with sodium borodeuteride to regenerate the alcohol. Use of both reactions sequences yield arteether containing two deuterium.