A tandem Prins spirocyclization for the stereoselective synthesis of tetrahydrospiro[chroman-2,4′-pyran] derivatives

Abstract

A novel cascade strategy has been developed for the synthesis of tetrahydrospiro[chroman-2,4′-pyran] derivatives by condensation of aldehydes with 2-(5-hydroxy-3-methylenepentyl)phenol. The reaction proceeds smoothly in the presence of BF₃·OEt₂ under mild conditions in a highly stereoselective manner leading to a single diastereomer. This approach is simple and convenient for the synthesis of pharmacologically relevant spirochroman scaffolds.