A Facile Synthesis of Dragmacidin B and 2,5-Bis(6‘-bromo-3‘-indolyl)piperazine

A Facile Synthesis of Dragmacidin B and 2,5-Bis(6‘-bromo-3‘-indolyl)piperazine

A short synthesis of dragmacidin B (1), 2,5-bis(6‘-bromo-3‘-indolyl)piperazine (2), and corresponding didebromo analogues 8 and 9 is described. The key steps involve the dimerization of oxotryptamines 4 and 11 to give bis(indolyl)pyrazines 5 and 12, which upon selective reduction and reductive methy...

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Veröffentlicht in:Organic letters 2000-10, Vol.2 (20), p.3185-3187
Hauptverfasser: Miyake, Fumiko Y, Yakushijin, Kenichi, Horne, David A
Format: Artikel
Sprache:eng
Schlagworte:
Animals
Indoles - chemical synthesis
Methylation
Oxidation-Reduction
Piperazines - chemical synthesis
Porifera - chemistry
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Zusammenfassung:A short synthesis of dragmacidin B (1), 2,5-bis(6‘-bromo-3‘-indolyl)piperazine (2), and corresponding didebromo analogues 8 and 9 is described. The key steps involve the dimerization of oxotryptamines 4 and 11 to give bis(indolyl)pyrazines 5 and 12, which upon selective reduction and reductive methylation with sodium cyanoborohydride afforded the requisite piperazine natural products.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0001970