Catalytic asymmetric total synthesis of ent-hyperforin

Abstract

(Figure Presented) Key to success: The first catalytic asymmetric total synthesis of ent-hyperforin (see picture) was accomplished by using a Diels-Alder reaction promoted by a chiral cationic iron catalyst (A; 96% ee, d.r. >33:1), a diastereoselective Claisen rearrangement (B; 12:1 selectivity), an intramolecular aldol reaction (C), and a vinylogous Pummerer rearrangement (D) as key steps. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.