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Synthesis 2011(24): 3991-3996  
DOI: 10.1055/s-0031-1289601
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Method for the Synthesis of Sulforaphane and Related Isothiocyanates

Xin Chen*a, Zhengyi Lib, Xiaoqiang Sunb, Hongzhao Mab, Xiaoxin Chenc, Jie Rena, Kun Hua
a School of Pharmaceutical & Life Sciences, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China
Fax: +86(519)86334598; e-Mail: xinchen@cczu.edu.cn;
b School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. of China
c Cancer Research Program, Julius L. Chambers Biomedical/Biotechnology Research Institute, North Carolina Central University, 700 George Street, Durham, NC 27707, USA
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Publication History

Received 21 August 2011
Publication Date:
11 November 2011 (online)

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Abstract

The biologically important isothiocyanate sulforaphane (4-isothiocyanatobutyl methyl sulfoxide) was synthesized in six simple steps from commercially available 4-aminobutan-1-ol with an overall yield of 64%. The new synthetic method is suitable for multigram-scale preparation of sulforaphane and does not require expensive or toxic reagents. A novel one-pot procedure was also developed for preparing isothiocyanates through reaction of amines with O-phenyl chlorothioformate under mild conditions. Additionally, methyl pyrrolidine-1-carbodithioate was obtained as an unexpected byproduct, and this protocol was shown to be useful for the synthesis of S-aryl or S-heterocyclic thiocarbamates with cyclic side chains.

Key words

isothiocyanates - thiocarbamates - sulforaphane - antitumor agents