A new glycociamidine ring precursor: syntheses of (Z)-hymenialdisine, (Z)-2-debromohymenialdisine, and (+/-)-endo-2-debromohymenialdisine.
[chemical reaction: see text]. The synthesis of the C11H5 marine sponge alkaloids, (Z)-hymenialdisine and (Z)-2-debromohymenialdisine, is described. A key step was the condensation between aldisine or its monobromo derivative and a new, efficient imidazolinone-based glycociamidine precursor. In the first case, the main product turned out to be the unprecedented (+/-)-endo-2-debromohymenialdisine.
Papeo
Gianluca
G
Department of Chemistry, BU-Oncology, Nerviano Medical Sciences, Viale Pasteur 10, 20014 Nerviano (MI), Italy. gianluca.papeo@nervianoms.com
Posteri
Helena
H
Borghi
Daniela
D
Varasi
Mario
M
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000818:Animals; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D008386:Marine Biology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D011758:Pyrroles; C097660:debromohymenialdisine; C107079:hymenialdisine