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; Steven A. 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, Steven A. Ward, Paul M. O'Neill

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 I₂ 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.

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
Externally published	Yes

Keywords

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

Access to Document

10.1016/j.bmcl.2008.01.053

Cite this

@article{2ccc426715484679991fffdffe749c08,

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 I2 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.",

keywords = "1,2,4-Trioxane, Antimalarial, Artemisinin, Plasmodium falciparum, Tetraoxane",

author = "Ellis, {Gemma L.} and Richard Amewu and Charlotte Hall and Karen Rimmer and Ward, {Steven A.} and O'Neill, {Paul M.}",

year = "2008",

month = mar,

day = "1",

doi = "10.1016/j.bmcl.2008.01.053",

language = "English",

volume = "18",

pages = "1720--1724",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd.",

number = "5",

}

TY - JOUR

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, Steven A.

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 I2 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.

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 I2 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.

KW - 1,2,4-Trioxane

KW - Antimalarial

KW - Artemisinin

KW - Plasmodium falciparum

KW - Tetraoxane

UR - http://www.scopus.com/inward/record.url?scp=39849083194&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2008.01.053

DO - 10.1016/j.bmcl.2008.01.053

M3 - Article

C2 - 18243702

AN - SCOPUS:39849083194

SN - 0960-894X

VL - 18

SP - 1720

EP - 1724

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

Access to Document

Other files and links

Fingerprint

Cite this