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Synthesis of 3β‐Hydroxy[21‐ 14 C]‐5β‐pregn‐8(14)‐en‐20‐one from Chenodeoxycholic Acid
Author(s) -
Deluca MóNica E.,
Seldes Alicia M.,
Gros Eduardo G.
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690810
Subject(s) - chemistry , chenodeoxycholic acid , side chain , stereochemistry , bile acid , organic chemistry , biochemistry , polymer
3β‐Hydroxy[21‐ 14 C]5β‐pregn‐8(14)‐en‐20‐one ( 17 ) was prepared from chenodeoxycholic acid ( 1a ). The synthetic sequence involved: ( i ) degradation of the bile‐acid side chain to an etianic acid; ( ii ) formation of the 8(14)‐double bond; ( iii ) inversion of the configuration at C(3); ( iv ) construction of the acetyl side chain at C(17) with the required isotopic label at C(21). Structures of all described products were confirmed by chemical and spectroscopic (IR, 1 H‐NMR, 13 C‐NMR, MS) methods.