Quantitative and stereospecific dihydroxylations of Δ5- steroids: A green synthesis of plant growth hormone intermediates

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[1] Li, Tao
[2] Li, Chunbao
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Li, C. (lichunbao@tju.edu.cn) | 1600年 / American Chemical Society卷 / 61期
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Dihydroxylated Δ5-steroids are key intermediates in preparing steroids bearing a 5α-hydroxy-6-oxo moiety; which are plant growth hormones. Quantitative and stereospecific dihydroxylations of Δ5-steroids have been realized; using H2O 2 catalyzed by KI and H2SO4 at 80 C in aqueous dioxane. The workup consisted only of concentrating the solvents and filtering the products; no chromatography was needed. The reaction conditions tolerate various functional groups on the Δ5-steroids. A mechanism for this reaction is proposed and the reason that the reaction is quantitative and stereospecific is explained. © 2013 American Chemical Society;
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