An oxidative entry into the amido trioxadecalin ring system
Related Experiment Video
Updated: Sep 26, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Jason C Rech1, Paul E Floreancig
1Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
Abstract:
The amido trioxadecalin ring system is a key structural component of the architecturally interesting anticancer and immunosuppressive agents of the mycalamide, theopederin, and onnamide families of natural products. We report a new entry into this structure in which a mixed acetal serves as a surrogate for a formaldehyde hemiacetal in an addition to an oxidatively generated acyliminium ion. The stereochemical outcome of this process can be explained by the conformational preferences of the product ring system. [reaction: see text]
Related Concept Videos
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Radical Autoxidation

