Divergent synthesis of two polycyclic frameworks containing tricyclic bridgehead carbon centers by gold-catalyzed cycloisomerization of o-cyclopropylidenemethyl-o′-alkynylbiaryls

Abstract

Compounds containing tricyclic bridgehead carbon centers are privileged structures in drug discovery. In this work, two different polycyclic scaffolds containing this substructure have been accessed by divergent gold-catalyzed cycloisomerizations of o-cyclopropylidenemethyl-o′-alkynylbiaryls. Selectivity towards one or the other scaffold is mainly controlled by temperature. The electronic nature of the arene group at the alkyne also plays a significant role, which is explained based on the proposed mechanism.

Graphical abstract: Divergent synthesis of two polycyclic frameworks containing tricyclic bridgehead carbon centers by gold-catalyzed cycloisomerization of o-cyclopropylidenemethyl-o′-alkynylbiaryls

Supplementary files

Article information

Article type
Research Article
Submitted
27 May 2025
Accepted
06 Aug 2025
First published
26 Aug 2025
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2025, Advance Article

Divergent synthesis of two polycyclic frameworks containing tricyclic bridgehead carbon centers by gold-catalyzed cycloisomerization of o-cyclopropylidenemethyl-o′-alkynylbiaryls

L. Sánchez-Jiménez, A. Gargantiel, M. A. Fernández-Rodríguez and P. García-García, Org. Chem. Front., 2025, Advance Article , DOI: 10.1039/D5QO00816F

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