Related Experiment Video
Updated: Jun 29, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Synthesis of the Tetracyclic Spiro-naphthoquinone Chartspiroton
Liesa Röder1, Klaus Wurst2, Thomas Magauer1
1Department of Organic Chemistry and Center for Molecular Biosciences, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria.
None:
Chartspiroton is a recently discovered naphthoquinone natural product that features a spiro-fused benzofuran lactone. We report its first synthesis via an 11-step linear sequence. The sterically hindered tetra-ortho-substituted biaryl subunit was installed by base-induced ring expansion of a readily available 1,3-indandione. This step also liberated the fully substituted naphthalene core unit at the same time. The unique spiro-fused benzofuran lactone of the natural product was constructed via late-stage oxidation of an advanced naphthoquinone.
More Related Videos
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Five-Membered Heterocyclic Aromatic Compounds: Overview
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Woodward–Hoffmann Selection Rules and Microscopic Reversibility
Thermal and Photochemical Electrocyclic Reactions: Overview
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation