Unknown

Dataset Information

0

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

Json Xml
altmetric image

Publications

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]

Similar Datasets

Unknown Synthesis and Study of the Antimalarial Cardamom Peroxide.
| S-EPMC6181145 | biostudies-literature
Unknown Antimalarial activity of primaquine operates via a two-step biochemical relay.
| S-EPMC6642103 | biostudies-literature
Unknown Four-Step Total Synthesis of (+)-Yaoshanenolides A and B.
| S-EPMC6644681 | biostudies-literature
Unknown Synthesis of indole-cycloalkyl[<i>b</i>]pyridine hybrids via a four-component six-step tandem process.
| S-EPMC6278771 | biostudies-literature
Unknown A one-step, atom economical synthesis of thieno[2,3-d]pyrimidin-4-amine derivatives via a four-component reaction.
| S-EPMC6922009 | biostudies-literature
Unknown A sequential strand-displacement strategy enables efficient six-step DNA-templated synthesis.
| S-EPMC3125949 | biostudies-literature
Unknown Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F.
| S-EPMC8159174 | biostudies-literature
Unknown Three-step synthesis of an annulated ?-carboline via palladium catalysis.
| S-EPMC3861870 | biostudies-literature
Unknown Galactan synthesis in a single step via oligomerization of monosaccharides.
| S-EPMC4273286 | biostudies-literature
Unknown Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy.
| S-EPMC4732274 | biostudies-literature