Two-Directional Synthesis of Polycyclopropanes. An Approach to the Quinquecyclopropane Fragment of U-106305
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Abstract
The stereoselective preparation of three stereoisomeric tercyclopropanes and a quinquecyclopropane was investigated. Two of the tercyclopropanes were C2-symmetric and were prepared efficiently through the two-directional application of Charette's reagent-stereocontrolled cyclopropanation methodology. The nonsymmetric tercyclopropane was prepared by an iterative one-directional application of the same reagent-mediated cyclopropanation method. It was shown that the reagent-controlled transformations are far more effective for the stereoselective preparation of the tercyclopropanes than are the reactions which rely upon the influence of the substrate stereocenters. A C2-symmetric quinquecyclopropane, which possesses the repeating trans-syn stereochemistry, was prepared by iterative application of the two-directional strategy.
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