title: A conceptually novel construction of the 6a-hydroxypterocarpan skeleton - Synthesis of (±)-variabilin.
abstract: A new access to the 6a-hydroxypterocarpan variabilin was established. Key step of this concise total synthesis is a challenging cyclization of a haloketone via halogen-metal exchange and subsequent intramolecular addition to the carbonyl function.
authors.affiliation: Fachrichtung Chemie und Lebensmittelchemie, Organische Chemie I, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
authors.forename: Philipp
authors.initials: P
authors.lastname: Ciesielski
authors.affiliation: Fachrichtung Chemie und Lebensmittelchemie, Organische Chemie I, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany. Electronic address: peter.metz@chemie.tu-dresden.de.
authors.forename: Peter
authors.initials: P
authors.lastname: Metz
mesh_terms: D001578:Benzopyrans / Q000737:chemistry*; D003500:Cyclization; D006219:Halogens / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D008670:Metals / Q000737:chemistry; D011506:Proteins / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C507789:6a-hydroxypterocarpan; D001578:Benzopyrans; D006219:Halogens; D006576:Heterocyclic Compounds, 4 or More Rings; D008670:Metals; D011506:Proteins; C100625:variabilin
keywords: 6a-hydroxypterocarpans; Flavonoids; Halogen–metal exchange; Variabilin