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Remote functionalization reactions in steroids: discovery and application.

Paul B Reese1

  • 1Department of Chemistry, The University of the West Indies, Mona, Kingston 7, Jamaica.

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This summary is machine-generated.

This review covers 2001-2022 advances in remote steroid functionalization, detailing methods like Schönecker oxidation and hypohalite reactions. These techniques enable the synthesis of complex, biologically active steroids.

Keywords:
Anti-cancerBiologically activeC-H insertionHydroxylationRegioselective activationRemote functionalizationSteroidSynthesis

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Steroid functionalization is crucial for generating biologically active compounds.
  • Selective modification of remote positions in steroids presents significant synthetic challenges.
  • Advances in catalysis and oxidation methods have expanded the possibilities for steroid modification.

Purpose of the Study:

  • To review methods for the functionalization of remote positions in steroids published between 2001 and 2022.
  • To highlight the application of these functionalization techniques in the synthesis of biologically active compounds.
  • To provide an overview of established and novel activation methods for remote steroid sites.

Main Methods:

  • Hydroxylation using manganese-, rhodium-, ruthenium-, and osmium-centered porphyrins with PIDA oxidant.
  • Hydroxylation using dioxiranes at tertiary centers.
  • Schönecker oxidation for selective C-12 functionalization.
  • Iron-catalyzed oxidation with hydrogen peroxide and acetic acid.
  • Suarez conditions (hypohalite reaction) for remote hydroxylation.
  • Rhodium-catalyzed decomposition of steroidal-3β-diazoacetates.
  • Chromium- and iron-based acetate catalysis.
  • Ketone irradiation and α-hydroxylation of ethers.

Main Results:

  • Successful hydroxylation at numerous remote positions (e.g., C-1, -5, -6, -7, -11, -12, -14, -15, -16, -17, -18, -19, -20, -24, -25) using various catalytic systems.
  • Development and application of the Schönecker oxidation for selective C-12 functionalization.
  • Synthesis of complex biologically active molecules including cyclopamine, cephalostatin-1, cortistatin A, and others, utilizing key functionalization steps.
  • Demonstration of hypohalite chemistry for C-18/C-19 functionalization in natural product synthesis.

Conclusions:

  • Significant progress has been made in the selective functionalization of remote steroid positions.
  • These advancements provide powerful tools for the synthesis of complex, biologically relevant steroid derivatives.
  • The reviewed methods offer diverse strategies for accessing novel steroidal compounds with potential therapeutic applications.