zaragozic-acid-c and glycolic-acid

Despite the prevalence of repeating subunits in chiral natural products, stereocontrolled oligomerization is a largely unexplored strategy for construction of carbon skeletal frameworks. This report describes the use of silyl glyoxylates as dipolar glycolic acid synthons in a controlled oligomerization reaction for the efficient construction of the squalene synthase inhibitor zaragozic acid C. This new methodology allows rapid, stereocontrolled formation of the carbon skeleton with a desirable protecting group scheme while minimizing functional group repair and oxidation state manipulations.

Topics: Bridged Bicyclo Compounds, Heterocyclic; Carbon; Chemistry, Organic; Farnesyl-Diphosphate Farnesyltransferase; Glycolates; Glyoxylates; Kinetics; Models, Chemical; Molecular Structure; Stereoisomerism