A facile synthesis of dragmacidin B and 2,5-bis(6 '-bromo-3 '-indolyl)piperazine

Authors
Miyake, FY Yakushijin, K Horne, DA
Citation
Fy. Miyake et al., A facile synthesis of dragmacidin B and 2,5-bis(6 '-bromo-3 '-indolyl)piperazine, ORG LETT, 2(20), 2000, pp. 3185-3187
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
20
Year of publication
2000
Pages
3185 - 3187
Database
ISI
SICI code
1523-7060(20001005)2:20<3185:AFSODB>2.0.ZU;2-#
Abstract
[GRAPHICS] A short synthesis of dragmacidin a (1), 2,5-bis(6'-bromo-3'-indolyl)piperaz ine (2), and corresponding didebromo analogues 8 and 9 is described. The ke y steps involve the dimerization of oxotryptamines 4 and 11 to give bis(ind olyl)pyrazines 5 and 12, which upon selective reduction and reductive methy lation with sodium cyanoborohydride afforded the requisite piperazine natur al products.