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Cellular Lipid Extraction for Targeted Stable Isotope Dilution Liquid Chromatography-Mass Spectrometry Analysis

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Hetero[3.1.1]propellanes.

Rebecca I Revie¹, Ayan Dasgupta¹, Yasmine Biddick¹

¹Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK.

Nature Chemistry

|February 25, 2026

Summary

This summary is machine-generated.

Researchers developed a unified synthesis for heterocyclic [3.1.1]propellanes, crucial precursors for novel drug design building blocks. These compounds enable the creation of diverse bridged bicyclic heterocycles with improved properties.

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Synthetic Chemistry

Background:

[n.1.1]Propellanes are vital precursors to bicyclo[n.1.1]alkanes, valued in drug design as benzene ring bioisosteres.
Heterocyclic analogues offer potential for superior physicochemical profiles compared to carbocyclic versions.

Purpose of the Study:

To develop a unified synthesis for heterocyclic [3.1.1]propellanes containing oxygen, nitrogen, and sulfur heteroatoms.
To explore the utility of these novel propellanes in synthesizing bridged bicyclic heterocycles.

Main Methods:

Synthesis of a common precursor via rhodium-catalyzed cyclopropanation on a multigram scale.
Development of distinct synthetic routes for hetero[3.1.1]propellanes, differing from carbocyclic analogues.
Radical ring-opening reactions of the synthesized hetero[3.1.1]propellanes.

Main Results:

Successful unified synthesis of a family of heterocyclic [3.1.1]propellanes.
Demonstrated distinct synthetic approaches compared to carbocyclic propellanes.
Generated a variety of bridged heterocycles through radical ring-opening reactions.

Conclusions:

The developed methods provide access to novel heterocyclic [3.1.1]propellanes.
These compounds serve as versatile precursors for drug discovery programs.
The synthesized bridged heterocycles possess high utility in medicinal chemistry.