Biomimetically inspired short access to the 2-aminoimidazole-fused tetracyclic core of (+/-)-dibromoagelaspongin.
A six-step synthesis of the tetracyclic core of the natural compound (+/-)-dibromoagelaspongin, isolated from Agelas sp. Sponge, was achieved from the commercially available 5-aminopentan-1-ol, 2-trichloroacetylpyrrole, and 2-aminopyrimidine. Following a biomimetic inspired approach, successive oxidative reactions including the final DMDO biomimetic oxidation gave the interesting triaminomethane-fused core.
Picon
Sylvain
S
Institut de Chimie des Substances Naturelles du CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Tran
Huu Dau Elise
HD
Martin
Marie-Thérèse
MT
Retailleau
Pascal
P
Zaparucha
Anne
A
Al-Mourabit
Ali
A
D047230:Agelas; D000818:Animals; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D007093:Imidazoles; D011083:Polycyclic Compounds; D011758:Pyrroles; C542416:dibromoagelaspongin; C014973:2-aminoimidazole