title: Clarifying the structure of granadaene: total synthesis of related analogue [2]-granadaene and confirmation of its absolute stereochemistry.
abstract: Streptococcus agalactiae is an important agent in the infection of neonates in the first world. One of the most extended methods for its identification is based on the detection of a characteristic red pigment in the patient samples, named [12]-granadaene (1). In this article, we present a modular and flexible approach to simple analogues of this ornithine rhamno-polyene 1 and the elucidation of the most important features of its structure: the absolute configuration at C-27, the stereochemistry of the anomeric center and the link of the amino acid ornithine to the rest of the structure.
authors.affiliation: Department of Organic Chemistry, Faculty of Sciences, University of Granada, C. U. Fuentenueva s/n, Granada, Spain.
authors.forename: Miguel
authors.initials: M
authors.lastname: Paradas
authors.forename: Rocío
authors.initials: R
authors.lastname: Jurado
authors.forename: Ali
authors.initials: A
authors.lastname: Haidour
authors.forename: Javier
authors.initials: J
authors.lastname: Rodríguez Granger
authors.forename: Antonio
authors.initials: A
authors.lastname: Sampedro Martínez
authors.forename: Manuel
authors.initials: M
authors.lastname: de la Rosa Fraile
authors.forename: Rafael
authors.initials: R
authors.lastname: Robles
authors.forename: José
authors.initials: J
authors.lastname: Justicia
authors.forename: Juan M
authors.initials: JM
authors.lastname: Cuerva
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009952:Ornithine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013292:Streptococcus agalactiae / Q000737:chemistry*
chemical_list: C578973:(12)-granadaene; D011090:Polyenes; D009952:Ornithine