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
Steroidsjournal_title
Steroidsauthors
Khripach VA,Zhabinskii VN,Konstantinova OV,Khripach NB,Antonchick AV,Antonchick AP,Schneider Bdoi
10.1016/j.steroids.2005.02.014subject
Has Abstractpub_date
2005-07-01 00:00:00pages
551-62issue
8eissn
0039-128Xissn
1878-5867pii
S0039-128X(05)00059-0journal_volume
70pub_type
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