Unified Synthesis of Eudesmanolides, Combining Biomimetic Strategies with Homogeneous Catalysis and Free-Radical Chemistry

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Unified Synthesis of Eudesmanolides, Combining Biomimetic Strategies with Homogeneous Catalysis and Free-Radical Chemistry

Barrero, Alejandro F; Rosales, Antonio; Cuerva, Juan M; Oltra, J. Enrique

Organic letters, 05/2003, Volume: 5, Issue: 11

Journal Article

A general procedure for the synthesis of both 12,6- and 12,8-eudesmanolides has been developed. The key step is the titanocene-catalyzed radical cyclization of accessible epoxygermacrolides. The novel reagent 2,4,6-trimethyl-1-trimethylsilylpyridinium chloride, both compatible with oxiranes and capable of regenerating Cp2TiCl2 from Cp2Ti(Cl)H and Cp2Ti(Cl)OAc, played an important role in the catalytic cycle leading to exocyclic alkenes.

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Barrero, Alejandro F | Rosales, Antonio | Cuerva, Juan M | Oltra, J. Enrique

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