Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen Stitching Strategy

作者:Hu Xirui; Maimone Thomas J*
来源:Journal of the American Chemical Society, 2014, 136(14): 5287-5290.
DOI:10.1021/ja502208z

摘要

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.

  • 出版日期2014-4-9