Formal Total Synthesis of (±)-Isoalantolactone
Wilma Olsson1,2, Johan Wennerberg1,2, Sebastian Clementson1
1Centre for Analysis and Synthesis, Department of Chemistry, Lund University, SE-221 00Lund, Sweden.
Abstract:
Herein, we report a concise formal synthesis of (±)-isoalantolactone through a six-step route to the advanced intermediate of Tada. The 5/6/6-fused eudesmanolide core is assembled through a SmI2-mediated reductive lactonization, while a late-stage acid-promoted sequence combines global deprotection, intramolecular aldol condensation, and thermodynamic stereochemical convergence to establish the required relative stereochemistry. Computational analysis supports thermodynamically controlled formation of the observed diastereomer and validates the overall synthetic design.
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
C–C Bond Formation: Aldol Condensation Overview


