Synthesis of [C6‐CH₃‐¹⁴C] and [C6‐CH₃‐³H₃]mitomycin C

Abstract

Abstract A facile synthesis of the title compounds 2 and 3 is described. The key intermediate in the synthesis, 6‐demethyl‐7,7‐(ethylenedioxy)‐6‐(phenylselenenyl)mitosane ( 4 ) was synthesized in five steps from mitomycin A. Treatment of 4 with [ 14 C]methyl iodide in the presence of K 2 CO 3 afforded the [ 14 C]‐labelled mitosane ( 5 ). The removal of the phenylselenenyl group of 5 and subsequent treatment of the resultant mitosane 7 with ammonia led to the desired [ 14 C]mitomycin C (MMC) ( 2 ) with specific activity of 50 mCi/mmol. Similarly, [ 3 H]‐labelled MMC ( 3 ) with highly specific activity of 78.4 Ci/mmol was obtained.