“…However, isomerization of triol 3 , which lacks the potentially labile 13 16,17-ketol functionality of 7 , was more promising. Despite the poor solubility of 3 and its sluggish rate of isomerization, reaction conditions were found to give 4 as the major product. , Semipreparative reverse-phase HPLC afforded 4 , 14 , and 15 , which were characterized by 2D NMR and NOE difference spectroscopy to confirm the regio- and stereochemical structure assignments. …”
[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.
“…However, isomerization of triol 3 , which lacks the potentially labile 13 16,17-ketol functionality of 7 , was more promising. Despite the poor solubility of 3 and its sluggish rate of isomerization, reaction conditions were found to give 4 as the major product. , Semipreparative reverse-phase HPLC afforded 4 , 14 , and 15 , which were characterized by 2D NMR and NOE difference spectroscopy to confirm the regio- and stereochemical structure assignments. …”
[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.
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