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Four-step synthesis of the antimalarial cardamom peroxide via an oxygen stitching strategy.

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.

SUBMITTER: Hu X

PROVIDER: S-EPMC4353017 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Four-step synthesis of the antimalarial cardamom peroxide via an oxygen stitching strategy.

Hu Xirui X Maimone Thomas J TJ

Journal of the American Chemical Society 20140327 14

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 generatio ...[more]

PMID: 24673099

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