Organic letters

Synthesis of ring B unsaturated estriols. Confirming the structure of a diagnostic analyte for Smith-Lemli-Opitz syndrome

LW Guo, CHL Shackleton, WK Wilson

Index: Guo, Li-Wei; Shackleton, Cedric H. L.; Wilson, William K. Organic Letters, 2001 , vol. 3, # 16 p. 2547 - 2550

Full Text: HTML

Citation Number: 5

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 ...