<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The first stereoselective and high‐yielding syntheses of (+)‐procyanidin A<sub>2</sub> (I) and (+)‐cinnamtannin B<sub>1</sub> (II) are achieved by exploiting dual activation of the electrophilic flavan units at C‐2 and C‐4, thus allowing catechin annulation with nucleophilic flavan units in a regio‐ and stereoselective manner.</p> </abstract>