Preparation and Synthetic Applications of 2-Halotryptamines:  Synthesis of Elacomine and Isoelacomine

Preparation and Synthetic Applications of 2-Halotryptamines:  Synthesis of Elacomine and Isoelacomine

The preparation of 2-halotryptamines from tryptamine is described. New stereoselective intramolecular iminium ion spirocyclization methodology for the construction of spiro[pyrrolidine-3,3‘-oxindoles] is outlined in synthetic studies of elacomine (1) and isoelacomine (2).

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Veröffentlicht in:Organic letters 2004-03, Vol.6 (5), p.711-713
Hauptverfasser: Miyake, Fumiko Y, Yakushijin, Kenichi, Horne, David A
Format: Artikel
Sprache:eng
Schlagworte:
Cyclization
Elaeagnaceae - chemistry
Indoles - chemical synthesis
Molecular Structure
Plant Roots - chemistry
Spiro Compounds - chemical synthesis
Stereoisomerism
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Zusammenfassung:The preparation of 2-halotryptamines from tryptamine is described. New stereoselective intramolecular iminium ion spirocyclization methodology for the construction of spiro[pyrrolidine-3,3‘-oxindoles] is outlined in synthetic studies of elacomine (1) and isoelacomine (2).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol030138x