Titanocene(III)‐Catalyzed 6‐exo Versus 7‐endo Cyclizations of Epoxypolyprenes: Efficient Control and Synthesis of Versatile Terpenic Building Blocks |
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Authors: | Dr. José Justicia Dr. Tania Jiménez Dr. Delia Miguel Rafael Contreras‐Montoya Dr. Rachid Chahboun Prof. Enrique Álvarez‐Manzaneda Daniel Collado‐Sanz Prof. Diego J. Cárdenas Dr. Juan M. Cuerva |
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Affiliation: | 1. Department of Organic Chemistry, Faculty of Science University of Granada, C. U. Fuentenueva s/n, 18071 Granada (Spain);2. Department of Organic Chemistry, Faculty of Sciences, Universidad Autónoma de Madrid, Tres Cantos, Madrid (Spain) |
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Abstract: | In this article, a complete study on the selectivity of titanocene(III) cyclization of epoxypolyprenes is presented. The requirements for the formation of six‐ or seven‐membered rings during these cyclizations are determined, taking into account the different substitution pattern in the epoxypolyprene precursor. Thus, a complete selectivity to 6‐exo or 7‐endo cyclization process has been achieved, yielding mono‐, bi‐, and even tricyclic compounds, constituting a new and efficient access to this type of derivative. Additionally, this procedure opens the possibility to prepare excellent building blocks for the synthesis of polycyclic compounds with a trisubstituted oxygenated function, which is present in several natural terpenes. |
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Keywords: | cyclic compounds cyclization natural products radicals titanium |
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