Prins-Type Cyclization Reactions in Natural Product Synthesis

Prins-type cyclization reactions proceed through the intramolecular addition of a π-nucleophile to an oxocarbenium ion or related species to generate a ring through carbon–carbon bond formation, often with excellent and predictable stereocontrol. The widespread presence of naturally occurring oxygen-containing heterocycles has made these reactions exceedingly valuable for total synthesis efforts. This microreview covers several common variations of Prins-type cyclizations and highlights their applicability to the total synthesis of natural products and analogs.