Two-Directional Synthesis of Polycyclopropanes. An Approach to the Quintacyclopropane Fragment of U-106305
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.
Department
Chemistry
Publication Date
3-1-1997
Journal Title
Journal of Organic Chemistry
Publisher
American Chemical Society
Digital Object Identifier (DOI)
10.1021/jo961136b
Document Type
Article
Recommended Citation
Two-Directional Synthesis of Polycyclopropanes. An Approach to the Quintacyclopropane Fragment of U-106305, McDonald, W. S. Verbicky, C. A., Zercher, C. K., J. Org. Chem. 1997, 62, 1215-1222.
Rights
Copyright © 1997 American Chemical Society