Synthesis of Ring B Unsaturated Estriols. Confirming the Structure of a Diagnostic Analyte for Smith−Lemli−Opitz Syndrome
- 17 July 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (16) , 2547-2550
- https://doi.org/10.1021/ol016224j
Abstract
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.Keywords
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