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Synthesis of mitomycin C labeled with mono-tritium at the C6 - methyl position

✍ Scribed by Yutaka Kanda; Shiro Akinaga; Masaji Kasai

Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
165 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A first preparation of mitomycin C specifically labeled with mono‐tritium at the C6‐methyl position is described. The key intermediate in the synthesis, 7,7‐ethylenedioxy‐6‐methylenemitosane (5) was made by treating 7,7‐ethylenedioxy‐6‐phenylselenomitosane (4) with meta‐chloroperbenzoic acid. Subsequent 1,4‐addition of [^3^H]hydride gave 7,7‐ethylenedioxymitosane labeled with tritium (6). Amination at C7 position and deacetylation of 1a‐aziridine nitrogen of 6 gave [C6‐CH~3~‐^3^H~1~] mitomycin C (2) with an overall yield of 15%. The specific activity of the final compound was 16.2 mCi/mmol with 13% tritium incorporation.

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