An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity

Gemma L. Ellis; Richard Amewu; Charlotte Hall; Karen Rimmer; Steve Ward; Paul M. O'Neill

doi:10.1016/j.bmcl.2008.01.053

An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity

Gemma L. Ellis, Richard Amewu, Charlotte Hall, Karen Rimmer, Steve Ward, Paul M. O'Neill

Tropical Disease Biology

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

Here we present an efficient route into synthetically challenging bridged 1,2,4,5-tetraoxanes. The key to the success of this route is the use of H2O2 and catalytic I-2 to form the gem-dihydroperoxide followed by a Ag2O mediated alkylation using 1,3-diiodopropane. Using this methodology a range of bridged tetraoxanes which display good in vitro antimalarial activity were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1720-1724
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	5
DOIs	https://doi.org/10.1016/j.bmcl.2008.01.053
Publication status	Published - 1 Mar 2008

Keywords

1,2,4-Trioxane
Antimalarial
Artemisinin
Plasmodium falciparum
Tetraoxane

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10.1016/j.bmcl.2008.01.053

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title = "An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity",

abstract = "Here we present an efficient route into synthetically challenging bridged 1,2,4,5-tetraoxanes. The key to the success of this route is the use of H2O2 and catalytic I-2 to form the gem-dihydroperoxide followed by a Ag2O mediated alkylation using 1,3-diiodopropane. Using this methodology a range of bridged tetraoxanes which display good in vitro antimalarial activity were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.",

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T1 - An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity

AU - Ellis, Gemma L.

AU - Amewu, Richard

AU - Hall, Charlotte

AU - Rimmer, Karen

AU - Ward, Steve

AU - O'Neill, Paul M.

PY - 2008/3/1

Y1 - 2008/3/1

N2 - Here we present an efficient route into synthetically challenging bridged 1,2,4,5-tetraoxanes. The key to the success of this route is the use of H2O2 and catalytic I-2 to form the gem-dihydroperoxide followed by a Ag2O mediated alkylation using 1,3-diiodopropane. Using this methodology a range of bridged tetraoxanes which display good in vitro antimalarial activity were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.

AB - Here we present an efficient route into synthetically challenging bridged 1,2,4,5-tetraoxanes. The key to the success of this route is the use of H2O2 and catalytic I-2 to form the gem-dihydroperoxide followed by a Ag2O mediated alkylation using 1,3-diiodopropane. Using this methodology a range of bridged tetraoxanes which display good in vitro antimalarial activity were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.

KW - 1,2,4-Trioxane

KW - Antimalarial

KW - Artemisinin

KW - Plasmodium falciparum

KW - Tetraoxane

U2 - 10.1016/j.bmcl.2008.01.053

DO - 10.1016/j.bmcl.2008.01.053

M3 - Article

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VL - 18

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 5

ER -

An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity

Abstract

Keywords

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