Lewis Acid-Catalyzed Divergent (4+3)/(4+2) Annulations of <i>o</i>-Quinone Methides with Bicyclo[1.1.0]butanes Lead to sp³-Rich Oxabicyclic Frameworks.

ABSTRACT: Benzannulation strategies that attach a planar arene ring to cyclic, saturated, three-dimensional bridged motifs are becoming valuable for drug discovery. Herein, a Lewis acid-catalyzed [4+3] annulation of in situ-generated o-QMs with bicyclo[1.1.0]butanes is developed. Reaction modulation further leveraged a telescoped [4+2] annulation of o-QMs with the in situ-formed cyclobutanes, leading to diversified sp³-rich oxabicyclic architectures. Overall, this study expands the scope for a new bioisosteric space for medicinal chemistry.

SUBMITTER: Mondal S 

PROVIDER: S-EPMC12836357 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature