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

[Image: see text] 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 hydr...

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Autores principales: Hu, Xirui, Maimone, Thomas J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4353017/
https://www.ncbi.nlm.nih.gov/pubmed/24673099
http://dx.doi.org/10.1021/ja502208z
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author Hu, Xirui
Maimone, Thomas J.
author_facet Hu, Xirui
Maimone, Thomas J.
author_sort Hu, Xirui
collection PubMed
description [Image: see text] 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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spelling pubmed-43530172015-03-20 Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen Stitching Strategy Hu, Xirui Maimone, Thomas J. J Am Chem Soc [Image: see text] 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. American Chemical Society 2014-03-20 2014-04-09 /pmc/articles/PMC4353017/ /pubmed/24673099 http://dx.doi.org/10.1021/ja502208z Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Hu, Xirui
Maimone, Thomas J.
Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen Stitching Strategy
title Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen Stitching Strategy
title_full Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen Stitching Strategy
title_fullStr Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen Stitching Strategy
title_full_unstemmed Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen Stitching Strategy
title_short Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen Stitching Strategy
title_sort four-step synthesis of the antimalarial cardamom peroxide via an oxygen stitching strategy
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4353017/
https://www.ncbi.nlm.nih.gov/pubmed/24673099
http://dx.doi.org/10.1021/ja502208z
work_keys_str_mv AT huxirui fourstepsynthesisoftheantimalarialcardamomperoxideviaanoxygenstitchingstrategy
AT maimonethomasj fourstepsynthesisoftheantimalarialcardamomperoxideviaanoxygenstitchingstrategy

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