Dipole-Transmissive 1,3-Dipolar Cycloadditions: Modular, Diversity-Oriented Synthesis of Polycyclic Alkaloid Scaffolds

This report establishes dipole-transmissive 1,3-dipolar cycloaddition methodology that enables the rapid, modular, and diastereoselective construction of privileged alkaloid scaffolds via a diversity-oriented synthetic strategy. In addition to furnishing assorted functionalized pyrrolizidine, indolizidine, quinolizidine, and pyrazoline frameworks from simple building blocks, these tools facilitated formal syntheses of alkaloid natural products isoretronecanol, elaeokanine A, and grandisine D.