Construction of the Lactone-Bridged Scaffold of Alstoscholactine through an Acid-Catalyzed Prins Cyclization/Lactonization Cascade

Described herein is an acid-catalyzed Prins cyclization/lactonization cascade reaction of malonate-tethered inol-3-ylmethanol-olefin substrates, which rapidly constructs the lactone-bridged scaffold of the monoterpenene indole alkaloid alstoscholactine. This reaction demonstrates a wide substrate scope and functional group tolerance, and a catalytic asymmetric reaction provides high enantioselectivity. This work provides a powerful method to access the key framework of alstoscholactine and supports the proposed plausible biogenetic pathway.