Four-Step
Synthesis of the Antimalarial Cardamom Peroxide
via an Oxygen Stitching Strategy
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Abstract
A four-step synthesis
of the antimalarial terpene cardamom peroxide,
a 1,2-dioxepane-containing natural product, is reported from (−)-myrtenal
and molecular oxygen. This highly concise route was guided by biosynthetic
logic and enabled by an unusual manganese-catalyzed, tandem hydroperoxidation
reaction. The absolute configuration of the cardamom peroxide is reported,
and its mode of fragmentation following Fe(II)-mediated endoperoxide
reduction is established. These studies reveal the generation of reactive
intermediates distinct from previously studied endoperoxide natural
products