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A facile and efficient synthesis of 14C-labelled sulforaphane

✍ Scribed by Christopher A. D'Souza; Shantu Amin; Dhimant Desai

Publisher
John Wiley and Sons
Year
2003
Tongue
French
Weight
118 KB
Volume
46
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Isothiocyanates have gained considerable attention for their role as potent chemopreventive agents. Sulforaphane, 1a (SFN), a naturally occurring isothiocyanate, was isotopically labelled in five steps starting from 3‐(methylthio)‐1‐propanol (2). Reacting 2 with tosyl chloride in the presence of Et~3~N yielded the tosylate 3. Gently refluxing 3 with K^14^CN in DMF gave the nitrile 4b. Reduction to the amine 5b was achieved using BH~3~‐THF. Oxidation with 30% hydrogen peroxide followed by treatment with thiophosgene yielded (±)[1‐^14^C]SFN, 1b. The overall radiochemical yield was 4.4% based on the starting K^14^CN. Copyright © 2003 John Wiley & Sons, Ltd.

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