Development of a Cationic Cascade Trailing into Piancatelli Rearrangement En Route to Skeletally Diverse Polycyclic
Manveer Patel1, Chenna Jagadeesh1, Abhijit Nandy2
1Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, Lucknow-226014, India.
Abstract:
The aza-Piancatelli rearrangement represents a powerful strategy for accessing complex cyclopentenones, starting from furan carbinols. We demonstrate herein the use of a noncanonical furan building block and show that this reaction can be effectively combined with an azaoxyallyl cation-centered process. This integration leads to elusive polycyclic scaffolds bearing multiple contiguous stereocenters. The H-bonding clusters of HFIP serve as the sole promoter, highlighting a rapid, diversity-oriented synthesis of cyclopentanoid architectures.
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