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Synthesis 2025; 57(06): 1153-1170
DOI: 10.1055/a-2360-8218
DOI: 10.1055/a-2360-8218
short review
Bioisosteres
Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly Functionalized Saturated (Bio)isosteres of Benzene Rings
Financial support from the Research Support Project for Life Science and Drug Discovery [Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)] (Grant JP22ama121040j0001) to Y.I. from the Japan Agency for Medical Research and Development (AMED) is gratefully acknowledged.
Abstract
Recently, many saturated bioisosteres of the benzene ring have been developed, and their applications in drug development have been evaluated. Most of these bioisosteres are caged hydrocarbons, which have rigid skeletons and three-dimensional spaces. Recent efforts to synthesize these caged hydrocarbons have enabled access to multi-functionalized congeners that are expected to be (bio)isosteres of multi-functionalized benzenes. This short review summarizes recently reported methods for obtaining multi-functionalized (typically more than disubstituted) caged hydrocarbons.
1 Introduction
2 Proposed Structures of Caged Hydrocarbons as Saturated (Bio)isosteres of the Benzene Ring: A Brief Summary
3 Access to Multi-functionalized Caged Hydrocarbons: De Novo Synthetic Approaches
3.1 Bicyclo[1.1.1]pentanes (BCPs)
3.2 Bicyclo[2.1.1]hexanes (BCHs)
3.3 Bicyclo[3.1.1]heptanes (BCHeps)
3.4 Others
4 Access to Multi-functionalized Caged Hydrocarbons: C–H Functionalization
5 Conclusion
Key words
bioisostere - caged hydrocarbons - de novo synthesis - C–H functionalization - radical functionalizationPublication History
Received: 07 June 2024
Accepted after revision: 04 July 2024
Accepted Manuscript online:
04 July 2024
Article published online:
29 July 2024
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