Total Synthesis of (±)‐Quebrachamine via [3+2] Cycloaddition and Efficient Chloroacetamide Photocyclization

The total synthesis of (±)‐quebrachamine has been completed in 13 linear steps and 17.8 % overall yield. The indole core was constructed via a formal [3+2] dipolar cycloaddition between a functionalized nitrile and donor‐acceptor cyclopropane, and the synthetically challenging nine‐membered ring was secured by an efficient chloroacetamide photocyclization.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)