Synthesis of Acovenosides: Cardiac Glycosides with Potent Antitumor Activities

Abstract

Acovenoside A (1), a cardiac glycoside featuring a unique L-acovenose at C-3 and a 1β,3β,14β-trihydroxy aglycone (namely, acovenosigenin A), shows promising antiproliferative activities. Herein, we report the synthesis of acovenoside A (1) together with a panel of its congeners. The synthesis features the stereoselective introduction of the 1β,14β-OH and C17-butenolide moieties starting from androstenedione (7) and gold(I)-catalyzed glycosylation with superarmed glycosyl ortho-alkynylbenzoates as donors.