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Fluorous-enhanced multicomponent reactions for making drug-like library scaffolds
1Fluorous Technologies, Inc., University of Pittsburgh Applied Research Center, 970 William Pitt Way, Pittsburgh, Pennsylvania 15238, USA. w.zhang@fluorous.com
Combinatorial Chemistry & High Throughput Screening
|March 10, 2007
Summary
Multicomponent reactions (MCRs) efficiently build complex molecules. Fluorous MCRs (F-MCRs) utilize fluorous tags for easy purification and further modifications, enabling diverse drug-like compound synthesis.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- Multicomponent reactions (MCRs) are efficient for synthesizing complex molecules.
- Post-MCR modifications enhance molecular complexity and diversity.
- MCRs are valuable in drug discovery and lead generation.
Purpose of the Study:
- To explore the utility of fluorous multicomponent reactions (F-MCRs) for generating molecular diversity.
- To demonstrate efficient post-F-MCR modifications and traceless tag removal.
- To synthesize novel heterocyclic and natural product-like scaffolds.
Main Methods:
- Utilizing fluorous tags on starting materials for selective isolation.
- Employing fluorous solid-phase extraction (F-SPE) for purification.
- Applying techniques like microwave irradiation and Ugi/de-Boc/cyclization, MCR/Suzuki coupling, and [3+2] cycloaddition/de-tag/cyclization protocols.
Main Results:
- Successful synthesis of diverse molecular scaffolds through F-MCRs.
- Efficient isolation and purification of fluorous intermediates using F-SPE.
- Demonstration of traceless fluorous tag removal to yield final products.
- Generation of unique heterocyclic and natural product-like libraries.
Conclusions:
- F-MCRs offer a powerful and efficient strategy for constructing complex molecules.
- Fluorous tagging and F-SPE facilitate purification and enable diverse post-MCR modifications.
- This approach is highly applicable to drug discovery and combinatorial chemistry efforts.
