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.
isothiocyanates - thiocarbamates - sulforaphane - antitumor agents
