title: Quantitative and stereospecific dihydroxylations of δ(5)-steroids: a green synthesis of plant growth hormone intermediates.
abstract: Dihydroxylated Δ(5)-steroids are key intermediates in preparing steroids bearing a 5α-hydroxy-6-oxo moiety, which are plant growth hormones. Quantitative and stereospecific dihydroxylations of Δ(5)-steroids have been realized, using H2O2 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 Δ(5)-steroids. A mechanism for this reaction is proposed and the reason that the reaction is quantitative and stereospecific is explained.
authors.affiliation: Department of Chemistry, School of Science, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, China.
authors.forename: Tao
authors.initials: T
authors.lastname: Li
authors.forename: Chunbao
authors.initials: C
authors.lastname: Li
mesh_terms: D055772:Green Chemistry Technology; D006900:Hydroxylation; D015394:Molecular Structure; D010937:Plant Growth Regulators / Q000138:chemical synthesis / Q000737:chemistry*; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D010937:Plant Growth Regulators; D013256:Steroids