Addition of Chiral Nucleophiles to Pyridine Compounds: Total Synthesis of (−)‐Isovallesiachotamine and (+)‐Vallesiachotamine

An enantiomerically pure skeleton of indol alkaloids can be constructed in a one-pot procedure by adding chiral nucleophiles such as lithiated 2 to the pyridinium compound 1 and carrying out the Pictet–Spengler ring closure according to Wenkert. The product of this reaction has five chiral centers and can be transformed into the title compounds in few steps.