Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids

Vladimir A. Khripach*, Vladimir N. Zhabinskii, Olga V. Konstantinova, Natalya B. Khripach, Alexey V. Antonchick, Andrey P. Antonchick, Bernd Schneider

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

23 Citations (Scopus)

Abstract

A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3β-hydroxy-Δ5- or a Δ4-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3β-acetoxy-pregn-5-en-20-carboxylic acid. The obtained compounds are useful as standards for studies of cholic acids. Construction of the side chain was achieved by linkage of steroidal 23-iodides to sulfones prepared from (2R)- and (2S)-3-hydroxy-2-methylpropanoates. Oxidation of intermediate 26-alcohols into the corresponding carboxylic acids ensuring preservation of stereochemistry at C-25 and functional groups in the cyclic part was achieved with sodium chlorite catalyzed by TEMPO and bleach.

Original languageEnglish
Pages (from-to)551-562
Number of pages12
JournalSTEROIDS
Volume70
Issue number8
DOIs
Publication statusPublished - 1 Jul 2005
MoE publication typeA1 Journal article-refereed

Keywords

  • 26-Hydroxycholesterol
  • Biosynthesis
  • Cholestenoic acids
  • Cholic acids

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