Stereoselective Synthesis of Complex Polycyclic Aziridines: Use of the Brønsted Acid-Catalyzed aza-Darzens Reaction to Prepare an Orthogonally Protected Mitomycin C Intermediate with Maximal Convergency

摘要

A concise synthesis of a highly functionalized intermediate lacking only C10 of the mitomycin backbone is described. The key to this development is the Brønsted acid-catalyzed aza-Darzens reaction used to forge the cis-aziridine. Additionally an oxidative ketalization fortuitously occurs during the quinone-enamine coupling step, leading to an orthogonally protected hydroquinone.