Synthesis of 2-Substituted Bicyclo[2.1.1]Hexan-1-ols via SmI2-Mediated Reductive Cyclization Reactions
Journal
Advanced Synthesis & Catalysis
Journal Volume
366
Journal Issue
22
Start Page
4747
End Page
4754
ISSN
1615-4150
1615-4169
Date Issued
2024-10-10
Author(s)
Abstract
The replacement of benzene rings with saturated bioisosteric counterparts is a key priority in drug discovery programs, and disubstituted bicyclo[2.1.1]hexanes have been recognized as flexible molecular scaffolds that could act as ortho-substituted benzene bioisosteres. In this study, we outline the synthesis of a wide range of 2-substituted bicyclo[2.1.1]hexan-1-ols, which have the potential to emulate ortho-phenolic derivatives, via SmI2-mediated reductive cyclization reactions. The synthetic utility of this methodology was exemplified by the preparation of several saturated analogs of pharmaceutically relevant compounds.
Subjects
Cyclization
C−C Bond Formation
Isostere
Samarium(II) Iodide
Synthetic Methods
SDGs
Publisher
Wiley
Type
journal article