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p-TsOH-Catalyzed one-pot transformation of di- and trihydroxy steroids towards diverse A/B-ring oxo-functionalization†

Abstract

Abstract A solid support-mediated p-TsOH-catalyzed milder transformative protocol is developed to furnish diverse ring-A and/or ring-B oxo-functionalized steroids. To flourish interesting isomers involving A/B-ring of the biomolecules in one-pot, only solid-supports (and not solution!) were effective. p-TsOH/SiO2-Oxidation of 4β,7α-hydroxycholesterol, the major oxysterol in human circulation, into a mixture of cholest-4-en-3-one, cholest-4-ene-3,6-dione and 5α-cholestane-3,6-dione was the starting endeavor to further the present scope. The reaction protocol was optimized in detail, and efforts toward the mechanistic understanding favoring the solid support were also evaluated, and a possible synergetic catalytic system involving p-TsOH and SiO2 is expected. Application of the novel methodology to 4β,7α-dihydroxy steroids results the desired diverse ketosteroids through oxidation/oxidative dehydration which generalizes the process as a facile multi-oxo-functionalization steroidal transformation.

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Publication details

The article was received on 28 May 2017, accepted on 11 Jul 2017 and first published on 12 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ01878A
Citation: New J. Chem., 2017, Accepted Manuscript
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    p-TsOH-Catalyzed one-pot transformation of di- and trihydroxy steroids towards diverse A/B-ring oxo-functionalization†

    A. Sarkar, J. Das and P. N. ghosh, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ01878A

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