A facile and efficient synthesis of 14 C‐labelled sulforaphane

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...

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Bibliographic Details
Published in:Journal of labelled compounds & radiopharmaceuticals 2003-08, Vol.46 (9), p.851-859
Main Authors: D'Souza, Christopher A., Amin, Shantu, Desai, Dhimant
Format: Article
Language:English
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Summary: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.
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.724