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

Xirui Hu | Zendy; Thomas J. Maimone | Zendy

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

Author(s) -

Xirui Hu,

Thomas J. Maimone

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja502208z

Subject(s) - chemistry , peroxide , natural product , combinatorial chemistry , tandem , terpene , absolute configuration , artemisinin , stereochemistry , organic chemistry , plasmodium falciparum , materials science , malaria , immunology , composite material , biology

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.

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