What question did this study set out to answer?

To evaluate the feasibility and regioselectivity of N-bromosuccinimide as an oxidizing agent on the hydroxyl groups of cholic acid.

December 1, 1949Journal of the American Chemical Society

Selective Oxidation with N-Bromosuccinimide. I. Cholic Acid

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Authors

LFLouis FieserBryn Mawr College SRS. RajagopalanM S Swaminathan Research Foundation

Discussion

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Implication

Experimental synthesis demonstrates selective oxidation of cholic acid using N-bromosuccinimide, highlighting targeted functional group modification in steroid chemistry.

Key Points

To evaluate the feasibility and regioselectivity of N-bromosuccinimide as an oxidizing agent on the hydroxyl groups of cholic acid.
Treated cholic acid and related bile acid derivatives with N-bromosuccinimide under controlled solvent conditions.
Isolated, purified, and structurally characterized the resulting partially and fully oxidized steroid derivatives.
N-bromosuccinimide selectively oxidizes specific secondary alcohol groups on the cholic acid nucleus.
The reaction enables controlled conversion to specific keto-bile acid derivatives without non-specific degradation of the steroid skeleton.

Cite This Study

Fieser et al. (1949) studied this question.

synapsesocial.com/papers/6a834201020f710cfbca9b02 https://doi.org/10.1021/ja01180a015

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December 1, 1949Journal of the American Chemical Society

Selective Oxidation with N-Bromosuccinimide. I. Cholic Acid

View Full Paper

Ask AI

Bookmark

Authors

LFLouis FieserBryn Mawr College SRS. RajagopalanM S Swaminathan Research Foundation

Discussion

Member takes

Implication

Experimental synthesis demonstrates selective oxidation of cholic acid using N-bromosuccinimide, highlighting targeted functional group modification in steroid chemistry.

Key Points

To evaluate the feasibility and regioselectivity of N-bromosuccinimide as an oxidizing agent on the hydroxyl groups of cholic acid.
Treated cholic acid and related bile acid derivatives with N-bromosuccinimide under controlled solvent conditions.
Isolated, purified, and structurally characterized the resulting partially and fully oxidized steroid derivatives.
N-bromosuccinimide selectively oxidizes specific secondary alcohol groups on the cholic acid nucleus.
The reaction enables controlled conversion to specific keto-bile acid derivatives without non-specific degradation of the steroid skeleton.

Cite This Study

Fieser et al. (1949) studied this question.

synapsesocial.com/papers/6a834201020f710cfbca9b02 https://doi.org/10.1021/ja01180a015

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