Oleocanthal and oleacein are known
for a wide range of beneficial
activities in human health and the prevention of diseases. The inability
to isolate significant and pure amounts of these natural compounds
and their demanding synthesis lead to the development of an efficient,
five-step, three-pot procedure. The synthesis is performed by a convenient
biomimetic approach, starting from oleuropein, an abundant raw material
in olive leaves, through the mixed anhydride of oleoside. The method
is stereocontrolled and provides an efficient approach to the synthesis
of various oleocanthal analogues; thus, a small library of four compounds
was prepared with 35–45% overall yield.
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