A chiral-pool-based approach to the core structure of (+)-hyperforin

Abstract

Asymmetric entry to the bicyclic core structure of (+)-hyperforin is presented. The developed synthetic strategy features a carefully orchestrated stereochemical relay from the single chiral center residing within (-)-Wieland-Miescher ketone and an intramolecular aldol reaction to cast the [3.3.1] bicyclic scaffold found in a diverse array of polycyclic polyprenylated acylphloroglucinols. Asymmetric entry to the bicyclic core structure of (+)-hyperforin is presented. The developed synthetic strategy features a carefully orchestrated stereochemical relay from the single chiral center residing within (-)-Wieland-Miescher ketone and an intramolecular aldol reaction to cast the [3.3.1] bicyclic scaffold found in a diverse array ofpolycyclic polyprenylated acylphloroglucinols. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.