Self-Consistent Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C via Controlled Oligomerization
- 3 December 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (51) , 17281-17283
- https://doi.org/10.1021/ja808347q
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.Keywords
This publication has 13 references indexed in Scilit:
- Total Syntheses of Zaragozic Acids A and C by a Carbonyl Ylide Cycloaddition StrategyChemistry – A European Journal, 2006
- Formal Total Synthesis of (+)‐Zaragozic Acid C through an Ireland–Claisen RearrangementAngewandte Chemie International Edition in English, 2006
- A General protocol for systematic synthesis designPublished by Springer Nature ,2006
- Three-Component Coupling Reactions of Silylglyoxylates, Alkynes, and Aldehydes: A Chemoselective One-Step Glycolate Aldol ConstructionJournal of the American Chemical Society, 2005
- Vanadium-Catalyzed Asymmetric Oxidation of α-Hydroxy Esters Using Molecular Oxygen as Stoichiometric OxidantJournal of the American Chemical Society, 2005
- Total Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C by a Carbonyl Ylide Cycloaddition StrategyAngewandte Chemie International Edition in English, 2003
- Cholesterol-modulating agents kill acute myeloid leukemia cells and sensitize them to therapeutics by blocking adaptive cholesterol responsesBlood, 2003
- Total Synthesis of (+)-Zaragozic Acid CThe Journal of Organic Chemistry, 2000
- Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase.Proceedings of the National Academy of Sciences, 1993
- The squalestatings, novel inhibitors of squalene synthase produced by a species of Phoma. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activity.The Journal of Antibiotics, 1992