Expedient synthesis of 17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate from prednisolone utilising a novel Mattox rearrangement

Steroids. 2013 Dec 11;78(12-13):1281-7. doi: 10.1016/j.steroids.2013.09.008. Epub 2013 Sep 27.

Abstract

A six step transformation of prednisolone to 17α,21-dihydroxy-9β,11β-epoxy-16α-amethylpregna-1,4-diene-3,20-dione 21-acetate has been achieved in 13% unoptimised yield. Novel conditions for effecting a Mattox rearrangement and double dehydration of prednisolone were identified. Enhanced knowledge on the oxidation of silyl Δ(19,20)-enol ethers and structural factors that impact the success of the oxidation are also presented.

Keywords: Conjugate addition; Mattox rearrangement; Oxidation of silyl enol ether.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glucocorticoids / chemical synthesis*
  • Oxidation-Reduction
  • Prednisolone / analogs & derivatives*
  • Prednisolone / chemical synthesis
  • Prednisolone / chemistry*

Substances

  • Glucocorticoids
  • Prednisolone