Efficient Route to the Pineal Hormone Melatonin by Radical-Based Indole Synthesis

Abstract

The hormone melatonin, which is known to have a range of important biological effects, has been prepared in a high-yielding route that features formation of the indole nucleus by radical cyclization. Mediation of the radical cyclization by tristrimethylsilylsilane (TTMSS) is more efficient than by N-ethylpiperidine hypophosphite.

Keywords:

• Melatonin
• Radical
• Synthesis
• Indole

Acknowledgments

We thank the “Stiftelsen Bengt Lundqvists minne” and the “C F Liljewalchs resestipendiefond” for a visiting fellowship (to S.B.), the Royal Society for a Leverhulme Senior Research Fellowship to (J.M.) and EPSRC Mass Spectrometry Service, Swansea for mass spectra.