Enantioselective synthesis for the (-)-antipode of the pyrazinone marine alkaloid, hamacanthin A.
J Org Chem
; 66(14): 4865-9, 2001 Jul 13.
Article
em En
| MEDLINE
| ID: mdl-11442418
A short enantioselective total synthesis for the (-)-antipode of the antifungal marine alkaloid, hamacanthin A, (6R)-3,6-bis(6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone, is described. This synthesis proceeds through the coupling of 3-indolyl-alpha-oxoacetyl chloride and 3-indolyl azidoethylamine, followed by intramolecular aza-Wittig type cyclization. A concise and useful approach for the synthesis of (1R)-1-(indol-3-yl)-2-azidoethylamine using the Sharpless asymmetric dihydroxylation reaction followed by stereospecific azidation is also presented.
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Base de dados:
MEDLINE
Assunto principal:
Pirazinas
/
Indóis
Idioma:
En
Ano de publicação:
2001
Tipo de documento:
Article