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

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...

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Bibliographic Details
Published inSynthetic communications Vol. 33; no. 20; pp. 3631 - 3641
Main Authors Thomson, Douglas W., Commeureuc, Aurélien G. J., Berlin, Stefan, Murphy, John A.
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 01.01.2003
Taylor & Francis
Subjects
Chemistry
Chemistry, Organic
Indole
Melatonin
Physical Sciences
Radical
Science & Technology
Synthesis
synthesis
indole
radical
ANALOGS
AGENTS
melatonin
TUBULIN
CYCLIZATION
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Summary: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.
ISSN:0039-7911
1532-2432
1532-2432
DOI:10.1081/SCC-120024751