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Abstract

The "lactone concept" has been efficiently employed for the
first atropo-enantioselective synthesis of knipholone and
related natural phenylanthraquinones. Besides the regio- and
stereoselective construction of the biaryl axis, another
important step was the "synthetically late" introduction of the
C-acetyl group, either by a Friedel-Crafts type acetylation or
by an ortho-selective Fries rearrangement first tested on
simplified model systems and subsequently applied to the highly
atroposelective preparation of the natural products and of
simplified analogs thereof for biotesting. The synthetic
availability of these natural biaryls, their precursors, and
their unnatural analogs permitted a broader investigation of
the antiplasmodial activities of these interesting biaryls.