Self-Consistent Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C via Controlled Oligomerization

Citations Over TimeTop 10% of 2008 papers

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.

Related Papers

• → SF₅-Synthons: Pathways to Organic Derivatives of SF₆(2005)31 cited
• → Cu(II)-Catalyzed [3 + 1 + 1 + 1] Cyclization of 1,3-Diketones and 2-Naphthols Using N,N-Dimethylethanolamine as a Dual Carbon Synthon for the Synthesis of 2H-Chromenes(2023)11 cited
• → Supramolecular Synthons: Will Giant Rigid Superspheres Do?(2016)16 cited
• → Mathematical Model of Synthon Reactions(1989)1 cited
• → ChemInform Abstract: Ethynylglycine Synthon, a Useful Precursor for the Synthesis of Biologically Active Compounds: an Update ‐ Part I: Preparations of Ethynylglycine Synthon(2015)