Oppenauer oxidation


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Oppenauer oxidation

[′äp·ə‚nau̇·ər ‚äk·sə′dā·shən]
(organic chemistry)
The oxidation of a primary or secondary hydroxyl compound to form the corresponding carbonyl compound; aluminum alkoxide and an excess amount of a carbonyl hydrogen acceptor, such as benzophenone or acetone, are required.
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Cholesterol was oxidized to 4-cholesten-3-one by Oppenauer oxidation. Subsequent treatment with ozone yielded 3,5-seco-4-nor-5-cholestanon-3-oic acid, which was converted to 4-methyl-4-aza-5-cholesten-3-one, an enamine lactam, by reaction under heat and pressure with methylamine.
Hypocholesterolemic 3[beta]-benzyl-4-methyl-4-aza-5[alpha]-cholestane methiodide (ND-354)

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