Debromodispacamides B and D: isolation from the marine sponge Agelas mauritiana and stereoselective synthesis using a biomimetic proline route.
New debromopyrrole-2-aminoimidazolones, debromodispacamide B (1) and debromodispacamide D (2) were isolated from the sponge Agelas mauritiana, collected in the Solomon Islands. A biomimetic one-step reaction from pseudopeptides 5 and 13 in presence of air oxygen and guanidine gave the chiral form of the natural product stereoselectively.
Vergne
Carine
C
Institut de Chimie des Substances Naturelles du CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Appenzeller
Jérôme
J
Ratinaud
Céline
C
Martin
Marie-Thérèse
MT
Debitus
Cécile
C
Zaparucha
Anne
A
Al-Mourabit
Ali
A
D047230:Agelas / Q000737:chemistry*; D000818:Animals; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D008386:Marine Biology; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism
D007093:Imidazoles; D011758:Pyrroles; C527921:debromodispacamide B; C527922:debromodispacamide D; C117197:imidazolone; D011392:Proline