Abstract
Concise syntheses of four tetrahydropyranyl diarylheptanoids isolated from Dioscorea villosa have been described. The key features include Prins cyclization to construct the tetrahydropyran cores, Keck asymmetric allylation, and Mitsunobu inversion. Optimization of the Prins cyclization conditions in order to minimize racemization has been described. Our syntheses also confirmed the absolute stereochemistry of the natural products.
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