Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome.
[structure: see text] Brief partial syntheses are described for ring B unsaturated estriols, which are candidate metabolites diagnostic for Smith-Lemli-Opitz syndrome prenatally. These steroids are also likely metabolites of the Premarin preparation used in estrogen replacement therapy. Equilin (8) was converted in three steps to 7-dehydroestriol, which was isomerized to 8-dehydroestriol. The simplicity of the transformations belies the lability of these previously inaccessible metabolites and their synthetic precursors.
Guo
L W
LW
Department of Biochemistry and Cell Biology, Rice University, Houston, Texas 77005, USA.
Shackleton
C H
CH
Wilson
W K
WK
D015415:Biomarkers; D004964:Estriol / Q000138:chemical synthesis* / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D007202:Indicators and Reagents; D019082:Smith-Lemli-Opitz Syndrome / Q000175:diagnosis*; D013056:Spectrophotometry, Ultraviolet
D015415:Biomarkers; D007202:Indicators and Reagents; D004964:Estriol