Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates

Abstract

Cyclic carbonates have long been considered relatively inert molecules acting as protecting groups in complex multistep synthetic routes. This study shows that a concise, yet modular synthesis of indolizidine and quinolizidine alkaloids can be developed from vinyl-substituted cyclic carbonate (VCC) intermediates. Through a highly stereoselective palladium-catalyzed allylic alkylation reaction, these alkaloid motifs can be assembled in four synthetic and only two column purification steps. The combined results help to further advance functionalized cyclic carbonates as useful and reactive intermediates in natural product synthesis.

Keywords: alkaloids; indolizidine; palladium; quinolizidine; vinyl cyclic carbonate.