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Updated: May 24, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Diverging pathways to topologically complex polycyclic bis-acetals and their ring system interchange
Rafael R Castillo1, Maurizio Aquino, Zoila Gandara
1Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, F-91198 Gif-sur-Yvette Cedex, France.
Abstract:
Carbinol-tethered octalin-diols (1), which differ only by the C11 configuration at the angular position, were transformed selectively to three types of structurally unrelated original scaffolds such as unsymmetrical octahydroanthracenes (5/7), furofuranes (6), or spirans (8/9) via a two-step protocol. The 11S* configuration ensures a C13-C4 Friedel-Crafts type C-C bonding (through an unprecedented oxidative cleavage-triggered domino process) while the 11R* configuration allows for a C13-C2 Marson-type Friedel-Crafts C-C bonding (through a nucleophilic acetal opening).
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