title: Self-consistent synthesis of the squalene synthase inhibitor zaragozic acid C via controlled oligomerization.
abstract: 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.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors.forename: David A
authors.initials: DA
authors.lastname: Nicewicz
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Satterfield
authors.forename: Daniel C
authors.initials: DC
authors.lastname: Schmitt
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D013186:Farnesyl-Diphosphate Farnesyltransferase / Q000037:antagonists & inhibitors*; D006016:Glycolates / Q000737:chemistry; D006038:Glyoxylates / Q000737:chemistry; D007700:Kinetics; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D006016:Glycolates; D006038:Glyoxylates; C079090:zaragozic acid C; C031149:glycolic acid; D002244:Carbon; D013186:Farnesyl-Diphosphate Farnesyltransferase