Organic letters

Unified synthesis of eudesmanolides, combining biomimetic strategies with homogeneous catalysis and free-radical chemistry

AF Barrero, A Rosales, JM Cuerva, JE Oltra

文献索引：Barrero, Alejandro F.; Rosales, Antonio; Cuerva, Juan M.; Oltra, J. Enrique Organic Letters, 2003 , vol. 5, # 11 p. 1935 - 1938

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被引用次数: 113

摘要

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.