A Practical Regioselective Synthesis of Alkylthio- or Arylthioindoles without the Use of Smelly Compounds Such as Thiols
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A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the <i>C</i><sup>3</sup>-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the <i>C</i><sup>2</sup>-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant <i>Staphylococcus aureus</i> (anti-MRSA) bromomethylthioindoles (MC 5–8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A.
- Chemical and Pharmaceutical Bulletin
Chemical and Pharmaceutical Bulletin 61(3), 292-303, 2013
The Pharmaceutical Society of Japan