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

Abstract:

:A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3beta-hydroxy-Delta(5)- or a Delta(4)-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3beta-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.

journal_name

Steroids

journal_title

Steroids

authors

Khripach VA,Zhabinskii VN,Konstantinova OV,Khripach NB,Antonchick AV,Antonchick AP,Schneider B

doi

10.1016/j.steroids.2005.02.014

subject

Has Abstract

pub_date

2005-07-01 00:00:00

pages

551-62

issue

8

eissn

0039-128X

issn

1878-5867

pii

S0039-128X(05)00059-0

journal_volume

70

pub_type

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