Synthesis of medium-sized heterocycles via cyclopropane fragmentation

CHED 236

Seth V. Kingree, kingresv@jmu.edu, Andrew S. D. Blanchard, Kerry E. O'Neil, and Kevin P. C. Minbiole, minbiokp@jmu.edu. Department of Chemistry, James Madison University, MSC 7701, Harrisonburg, VA 22807
A cyclopropanol fragmentation approach to the synthesis of oxygen-containing heterocycles has been developed. This strategy condenses cyclopropyl diols with aldehydes to form an acetal, which is subsequently rearranged to furnish a keto-oxepane. Efforts to extend this methodology to multiple ring sizes and substitution patterns are presented.