7-e ndo Radical Cyclizations Catalyzed by Titanocene (III). Straightforward Synthesis of Terpenoids with Seven-Membered Carbocycles

J Justicia, JL Oller-López, AG Campana…

Index: Justicia, Jose; Oller-Lopez, Juan L.; Campana, Araceli G.; Oltra, J. Enrique; Cuerva, Juan M.; Bunuel, Elena; Cardenas, Diego J. Journal of the American Chemical Society, 2005 , vol. 127, # 42 p. 14911 - 14921

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Citation Number: 112

Abstract

We describe a novel procedure for the straightforward synthesis of seven-membered carbocycles via free-radical chemistry, based on titanocene (III)-catalyzed 7-endo-dig and 7- endo-trig cyclizations. This procedure has proved to be useful for the chemical preparation of terpenoids with different skeletons containing cycloheptane rings, including the first total syntheses of dauca-4 (11), 8-diene (2), barekoxide (3), authentic laukarlaol (81), and a ...