Synthesis of 1-Substituted Bicyclo[2.1.1]hexan-2-ones via a Sequential SmI₂-Mediated Pinacol Coupling and Acid-Catalyzed Pinacol Rearrangement Reaction.

ABSTRACT: A two-step procedure, combining a SmI₂-mediated transannular pinacol coupling reaction with an acid-catalyzed pinacol rearrangement process, was employed to prepare a diverse range of 1-substituted bicyclo[2.1.1]hexan-5-ones from cyclobutanedione derivatives. To underscore the significance of these bicyclic ketones in drug synthesis, an sp³-rich analog of nitazoxanide, a well-known antiparasitic and antiviral agent, was synthesized.

SUBMITTER: Lee YC 

PROVIDER: S-EPMC11536404 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature