Concise synthesis of didebromohamacanthin A and demethylaplysinopsine: addition of ethylenediamine and guanidine derivatives to the pyrrole-amino acid diketopiperazines in oxidative conditions.
Oxidative nucleophilic addition of ethylenediamine and guanidine derivatives to pyrrole-amino acid diketopiperazines was shown to provide substituted 5,6-dihydro-2(1H)-piperazinones, quinoxalinones, and 2-aminoimidazolones. On the basis of this methodology, a concise approach to natural products didebromohamacanthin A and demethylaplysinopsine has been demonstrated.
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, CNRS , 91198 Gif-sur-Yvette Cedex, France.
Ludmila
L
Ermolenko
Hu
H
Zhaoyu
Clarisse
C
Lejeune
Carine
C
Vergne
Céline
C
Ratinaud
Thanh Binh
TB
Nguyen
Ali
A
Al-Mourabit
D000596:Amino Acids / Q000737:chemistry*; D054659:Diketopiperazines / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry*; D019791:Guanidine / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
C585606:6''-debromohamacanthin A; D000596:Amino Acids; D054659:Diketopiperazines; D005029:Ethylenediamines; D026121:Indole Alkaloids; D011758:Pyrroles; C000590473:demethylaplysinopsine; C031234:ethylenediamine; D019791:Guanidine