Related Experiment Video
Updated: Apr 8, 2026

Structural Biology and Analytical Chemistry Approaches for Characterizing C-Glycoside Metabolic Enzymes in Human Gut Microbiota
Published on: May 23, 2025
Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification
Chia-Fu Chang1, Eric Stefan1, Richard E Taylor2
1Warren Family Research Center for Drug Discovery and Development and the Department of Chemistry & Biochemistry, 250 Nieuwland Science Hall, University of Notre Dame, Notre Dame, IN 46556-5670 (USA).
Abstract:
Lyngbyaloside C, a classic macrolide, isolated from Lyngbya bouilloni, has shown moderate anticancer activity against several cancer cell lines. Here, we report the first total synthesis and stereochemical configuration reassignment of lyngbyaloside C. The synthesis highlights a one-pot intermolecular ketene esterification reaction to form the crucial tertiary ester and tetrahydropyran. In addition, a novel and concise synthetic pathway towards the 1,3-syn secondary, tertiary diol fragment is described using a regio- and stereospecific electrophilic ether transfer reaction.
More Related Videos
Related Concept Videos
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
Formation of Lipopolysaccharides
Biosynthesis of Lipids
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Biosynthesis of Polysaccharides
Peptidoglycan Synthesis

