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 Et3N yielded the tosylate 3. Gently refluxing 3 with K 14CN in DMF gave the nitrile 4b. Reduction to the amine 5b was achieved using BH3-THF. Oxidation with 30% hydrogen peroxide followed by treatment with thiophosgene yielded (±)[1-14C]SFN, 1b. The overall radiochemical yield was 4.4% based on the starting K 14CN.
Original language | English (US) |
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Pages (from-to) | 851-859 |
Number of pages | 9 |
Journal | Journal of Labelled Compounds and Radiopharmaceuticals |
Volume | 46 |
Issue number | 9 |
DOIs | |
State | Published - Aug 2003 |
All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Biochemistry
- Radiology Nuclear Medicine and imaging
- Drug Discovery
- Spectroscopy
- Organic Chemistry