Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore [Letter]

Paul M. O'Neill; Amira Mukhtar; Steve Ward; Jamie F. Bickley; Jill Davies; Mario D. Bachi; Paul A. Stocks

doi:10.1021/ol0492142

Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore [Letter]

Paul M. O'Neill, Amira Mukhtar, Steve Ward, Jamie F. Bickley, Jill Davies, Mario D. Bachi, Paul A. Stocks

Tropical Disease Biology

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

67 Citations (Scopus)

Abstract

Thiol-olefin co-oxygenation (TOCO) of substituted allylic alcohols generates alpha-hydroxyperoxides that can be condensed in situ with various ketones to afford a series of functionalized 1,2,4-trioxanes in good yields. Manipulation of the phenylsulfenyl group in 4a allows for convenient modification to the spiro-trioxane substituents, and we describe, for the first time, the preparation of a new class of antimalarial prodrug.

Original language	English
Pages (from-to)	3035-3038
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	18
DOIs	https://doi.org/10.1021/ol0492142
Publication status	Published - 2 Sept 2004

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title = "Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore [Letter]",

abstract = "Thiol-olefin co-oxygenation (TOCO) of substituted allylic alcohols generates alpha-hydroxyperoxides that can be condensed in situ with various ketones to afford a series of functionalized 1,2,4-trioxanes in good yields. Manipulation of the phenylsulfenyl group in 4a allows for convenient modification to the spiro-trioxane substituents, and we describe, for the first time, the preparation of a new class of antimalarial prodrug.",

author = "O'Neill, \{Paul M.\} and Amira Mukhtar and Steve Ward and Bickley, \{Jamie F.\} and Jill Davies and Bachi, \{Mario D.\} and Stocks, \{Paul A.\}",

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T1 - Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore [Letter]

AU - O'Neill, Paul M.

AU - Mukhtar, Amira

AU - Ward, Steve

AU - Bickley, Jamie F.

AU - Davies, Jill

AU - Bachi, Mario D.

AU - Stocks, Paul A.

PY - 2004/9/2

Y1 - 2004/9/2

N2 - Thiol-olefin co-oxygenation (TOCO) of substituted allylic alcohols generates alpha-hydroxyperoxides that can be condensed in situ with various ketones to afford a series of functionalized 1,2,4-trioxanes in good yields. Manipulation of the phenylsulfenyl group in 4a allows for convenient modification to the spiro-trioxane substituents, and we describe, for the first time, the preparation of a new class of antimalarial prodrug.

AB - Thiol-olefin co-oxygenation (TOCO) of substituted allylic alcohols generates alpha-hydroxyperoxides that can be condensed in situ with various ketones to afford a series of functionalized 1,2,4-trioxanes in good yields. Manipulation of the phenylsulfenyl group in 4a allows for convenient modification to the spiro-trioxane substituents, and we describe, for the first time, the preparation of a new class of antimalarial prodrug.

U2 - 10.1021/ol0492142

DO - 10.1021/ol0492142

M3 - Letter

SN - 1523-7060

VL - 6

SP - 3035

EP - 3038

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore [Letter]

Abstract

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