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Sterol metabolism, XXXI. Synthesis of the epimeric [24‐ 3 H] cholest‐5‐ENE‐3β, 24‐diols
Author(s) -
Lin Yong Yeng,
Smith Leland L.
Publication year - 1974
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590100404
Subject(s) - epimer , ene reaction , yield (engineering) , chemistry , diol , stereochemistry , circular dichroism , organic chemistry , physics , thermodynamics
A synthesis of [24‐ 3 H] (24S)‐cholest‐5‐ene‐3β, 24‐diol (cerebrosterol) in 12.1% radiochemical yield and of its 24‐epimer has been achieved by sodium borotritide reduction of 3β‐hydroxycholest‐5‐en‐24‐one derived from 3β‐hydroxychol‐5‐enic acid by an improved procedure. The epimeric 3β, 24 diols were separated as the dibenzoate esters, for which circular dichroism data are presented in support of the assigned absolute stereochemistry.