title: Synthesis of (±)-aureol by bioinspired rearrangements.
abstract: A bioinspired and sustainable procedure for the straightforward synthesis of (±)-aureol has been achieved in eight steps (14% overall yield) from epoxyfarnesol. The key steps are the titanocene(III)-catalyzed radical cascade cyclization of an epoxyfarnesol derivative and a biosynthetically inspired sequence of 1,2-hydride and methyl shifts.
authors.affiliation: Department of Organic Chemistry, Faculty of Sciences, University of Granada , 18071 Granada, Spain.
authors.forename: Antonio
authors.initials: A
authors.lastname: Rosales
authors.forename: Juan
authors.initials: J
authors.lastname: Muñoz-Bascón
authors.forename: Esther
authors.initials: E
authors.lastname: Roldan-Molina
authors.forename: Nazaret
authors.initials: N
authors.lastname: Rivas-Bascón
authors.forename: Natalia M
authors.initials: NM
authors.lastname: Padial
authors.forename: Roman
authors.initials: R
authors.lastname: Rodríguez-Maecker
authors.forename: Ignacio
authors.initials: I
authors.lastname: Rodríguez-García
authors.forename: J Enrique
authors.initials: JE
authors.lastname: Oltra
mesh_terms: D001669:Biochemical Phenomena; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D005204:Farnesol / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D009942:Organometallic Compounds; D012717:Sesquiterpenes; C455540:aureol; C406884:titanocene; D005204:Farnesol