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An atom efficient synthesis of tamoxifen
Dorus Heijnen1, Milan van Zuijlen1, Filippo Tosi1
1Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands. b.l.feringa@rug.nl.
Organic & Biomolecular Chemistry
|February 7, 2019
Summary
Direct carbolithiation of diphenylacetylenes enables efficient synthesis of the breast cancer drug tamoxifen. This novel palladium nanoparticle catalyst achieves high selectivity and yield in just two steps.
Area of Science:
- Organic Chemistry
- Catalysis
- Medicinal Chemistry
Background:
- Diphenylacetylenes are versatile organic building blocks.
- Efficient synthesis of tamoxifen is crucial for breast cancer treatment.
- Palladium-catalyzed cross-coupling reactions are vital in organic synthesis.
Purpose of the Study:
- To develop a direct carbolithiation method for diphenylacetylenes.
- To utilize the resulting alkenyllithium reagents in cross-coupling reactions.
- To synthesize tamoxifen efficiently using a novel catalytic system.
Main Methods:
- Direct carbolithiation of diphenylacetylenes.
- Palladium nanoparticle-catalyzed cross-coupling of alkenyllithium reagents.
- Synthesis of tamoxifen from commercially available starting materials.
Main Results:
- Achieved high (Z/E) selectivity (10:1) in the cross-coupling reaction.
- Obtained good yields of tamoxifen in only two steps.
- Demonstrated excellent atom economy and reaction mass efficiency.
Conclusions:
- The developed method provides an efficient and sustainable route to tamoxifen.
- The novel palladium nanoparticle catalyst is highly active and selective.
- This approach offers a significant advancement in the synthesis of tamoxifen and related compounds.
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