title: Biomimetically inspired short access to the 2-aminoimidazole-fused tetracyclic core of (+/-)-dibromoagelaspongin.
abstract: 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.
authors.affiliation: Institut de Chimie des Substances Naturelles du CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Picon
authors.forename: Huu Dau Elise
authors.initials: HD
authors.lastname: Tran
authors.forename: Marie-Thérèse
authors.initials: MT
authors.lastname: Martin
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Anne
authors.initials: A
authors.lastname: Zaparucha
authors.forename: Ali
authors.initials: A
authors.lastname: Al-Mourabit
mesh_terms: 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
chemical_list: D007093:Imidazoles; D011083:Polycyclic Compounds; D011758:Pyrroles; C542416:dibromoagelaspongin; C014973:2-aminoimidazole