Synthesis of a structurally constrained endoperoxide having antimalarial activity from α-santonin

C. W. Van Der Westhuyzen; C. J. Parkinson

Synthesis of a structurally constrained endoperoxide having antimalarial activity from α-santonin

C. W. Van Der Westhuyzen, C. J. Parkinson

Dentistry and Medical Sciences

CSIR Bio/Chemtek

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

3 Citations (Scopus)

Abstract

α-Santonin 3 was successfully converted into a biologically active compound 5b containing an endoperoxide group through a photo-oxygenation approach as a single isomer. It was found that the singlet oxygen afforded the isomer produced by attack from the sterically-hindered face of cyclohexadiene derivative 4. Evidence to this end is presented based on NOE results and the products formed in the photo-oxygenation reaction, as well as the in vitro testing of 5b for antimalarial activity.

Original language	English
Pages (from-to)	41-45
Number of pages	5
Journal	South African Journal of Chemistry
Volume	58
Publication status	Published - 14 Feb 2005

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title = "Synthesis of a structurally constrained endoperoxide having antimalarial activity from α-santonin",

abstract = "α-Santonin 3 was successfully converted into a biologically active compound 5b containing an endoperoxide group through a photo-oxygenation approach as a single isomer. It was found that the singlet oxygen afforded the isomer produced by attack from the sterically-hindered face of cyclohexadiene derivative 4. Evidence to this end is presented based on NOE results and the products formed in the photo-oxygenation reaction, as well as the in vitro testing of 5b for antimalarial activity.",

keywords = "Endoperoxide, Photo-oxygenation, Santonin, Singlet oxygen",

author = "{Van Der Westhuyzen}, {C. W.} and Parkinson, {C. J.}",

year = "2005",

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T1 - Synthesis of a structurally constrained endoperoxide having antimalarial activity from α-santonin

AU - Van Der Westhuyzen, C. W.

AU - Parkinson, C. J.

PY - 2005/2/14

Y1 - 2005/2/14

N2 - α-Santonin 3 was successfully converted into a biologically active compound 5b containing an endoperoxide group through a photo-oxygenation approach as a single isomer. It was found that the singlet oxygen afforded the isomer produced by attack from the sterically-hindered face of cyclohexadiene derivative 4. Evidence to this end is presented based on NOE results and the products formed in the photo-oxygenation reaction, as well as the in vitro testing of 5b for antimalarial activity.

AB - α-Santonin 3 was successfully converted into a biologically active compound 5b containing an endoperoxide group through a photo-oxygenation approach as a single isomer. It was found that the singlet oxygen afforded the isomer produced by attack from the sterically-hindered face of cyclohexadiene derivative 4. Evidence to this end is presented based on NOE results and the products formed in the photo-oxygenation reaction, as well as the in vitro testing of 5b for antimalarial activity.

KW - Endoperoxide

KW - Photo-oxygenation

KW - Santonin

KW - Singlet oxygen

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JO - South African Journal of Chemistry

JF - South African Journal of Chemistry

ER -

Synthesis of a structurally constrained endoperoxide having antimalarial activity from α-santonin

Abstract

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