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05:15
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Enriching chemical space with diversity-oriented synthesis
Gemma L Thomas1, Emma E Wyatt, David R Spring
1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
Current Opinion in Drug Discovery & Development
|November 23, 2006
Summary
Discovering new molecular entities for drug discovery and chemical genetics relies on screening diverse small molecule collections. Designing and synthesizing these collections presents a significant challenge for synthetic chemists, with recent strategies addressing the chemical space interrogated.
Area of Science:
- Medicinal Chemistry
- Chemical Biology
- Synthetic Organic Chemistry
Background:
- Drug discovery and chemical genetics necessitate screening diverse, high-quality small molecule libraries.
- The creation of such molecular collections is a complex task for synthetic chemists.
- Understanding the chemical space explored by these collections is crucial.
Purpose of the Study:
- To present recent strategies and findings in the design and synthesis of diverse small molecule collections.
- To contextualize these efforts within the scope of the chemical space being interrogated.
- To address the challenges faced by synthetic chemists in generating these essential resources.
Main Methods:
- Review of recent synthetic strategies for small molecule library generation.
- Analysis of structural diversity within compound collections.
- Mapping of collections to relevant chemical space.
Main Results:
- Highlighting successful approaches to synthesizing structurally diverse small molecules.
- Demonstrating the interrogation of broad chemical space through strategic library design.
- Presenting key outcomes from recent efforts in collection development.
Conclusions:
- Effective strategies exist for the design and synthesis of diverse small molecule collections.
- These collections are vital for advancing drug discovery and chemical genetics.
- Continued innovation in synthetic chemistry is key to expanding accessible chemical space.
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Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.