text: Although not well understood at the time, the Fürst-Plattner rule played a critical role during R. B. Woodward's synthesis of Reserpine. The problematic stereocenter is highlighted in red, below.
  Woodward's synthetic strategy used a Bischler-Napieralski reaction to form the tetrahydrocarbazole portion of Reserpine.  The subsequent imine intermediate was treated with sodium borohydride, affording the wrong stereoisomer due to the Fürst-Plattner effect.
  Examining the intermediate structure shows that the hydride preferentially added to the 3-carbon via the top face of the imine to avoid an unfavorable twist-boat intermediate.  Unfortunately, this outcome required Woodward to perform several additional steps to complete the total synthesis of reserpine with the proper stereochemistry.