title: Syntheses of pseudoceramines A-D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges.
abstract: Herein we report the total syntheses of pseudoceramine A-D (2-5) and spermatinamine (1) isolated from the marine sponge Pseudoceratina sp. Direct acyl substitution of α-hydroxyiminoesters with amine nucleophiles was developed as a key transformation. The synthetic compounds confirm the reported structures and importantly gives access to non-symmetrical spermine based natural products carrying two different bromotyrosine building blocks. Our new synthesis of spermatinamine is two steps shorter and more efficient than the previously reported sequence.
authors.affiliation: Umeå Centre for Microbial Research, Department of Chemistry, Umeå University, SE-60187, Umeå, Sweden.
authors.forename: J Mikael
authors.initials: JM
authors.lastname: Hillgren
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Oberg
authors.forename: Mikael
authors.initials: M
authors.lastname: Elofsson
mesh_terms: D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013096:Spermine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D001688:Biological Products; C475724:bromotyrosine; C572229:pseudoceramine A; C572230:pseudoceramine B; C525803:spermatinamine; D013096:Spermine; D014443:Tyrosine