title: Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone.
abstract: A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported.
authors.affiliation: School of Chemistry & Physics, University of Adelaide , Adelaide 5005, South Australia, Australia.
authors.forename: Henry P
authors.initials: HP
authors.lastname: Pepper
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Tulip
authors.forename: Yuji
authors.initials: Y
authors.lastname: Nakano
authors.forename: Jonathan H
authors.initials: JH
authors.lastname: George
mesh_terms: D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001577:Benzophenones; D001688:Biological Products; D011083:Polycyclic Compounds; C577393:doitunggarcinone A; C579594:garcibracteatone