Copper-Catalyzed Stille Cross-Coupling Reaction and Application in the Synthesis of the Spliceostatin Core Structure
| Autor: | Arun K. Ghosh, Melissa S. Jurica, Joshua R. Born, Anne M. Veitschegger |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Allylic rearrangement
Diene 010405 organic chemistry Organic Chemistry Sulfolene Tetrahydropyran 010402 general chemistry 01 natural sciences Combinatorial chemistry Coupling reaction Article Catalysis 0104 chemical sciences Stille reaction chemistry.chemical_compound chemistry Achmatowicz reaction Copper Palladium |
| Zdroj: | J Org Chem |
| Popis: | An efficient palladium-free Stille cross-coupling reaction of allylic bromides and functionalized organostannylfuran using catalytic copper halide has been developed. The coupling reaction was optimized using CuI and low catalyst loading (down to 5 mol %). The reaction was conveniently carried out at ambient temperature in the presence of inorganic base to afford the coupling product in good-to-excellent yields. The utility of this reaction was demonstrated in the synthesis of a furan with sensitive functionalities. A sulfolene moiety was utilized as a masking group for the sensitive diene. Noyori asymmetric reduction, Achmatowicz reaction, and Kishi reduction steps converted sulfolene to a highly substituted tetrahydropyran intermediate used in the synthesis of the highly potent antitumor agents, spliceostatins, and their derivatives. |
| Databáze: | OpenAIRE |
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