title: Enantioselective Total Synthesis and Structure Confirmation of the Natural Dimeric Tetrahydroxanthenone Dicerandrol C.
abstract: The first enantioselective total synthesis of natural dicerandrol C (1 c) as its enantiomer containing a dimeric tetrahydroxanthenone skeleton is described starting from the enantiopure chromane 6 which was obtained through a Wacker-type cyclization with >99 % ee. For the formation of the dimeric skeleton a palladium-catalyzed Suzuki reaction was used. The synthesis allowed the confirmation of the absolute configuration of the dicerandrols.
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.
authors.forename: Dhandapani
authors.initials: D
authors.lastname: Ganapathy
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.
authors.forename: Johannes R
authors.initials: JR
authors.lastname: Reiner
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.
authors.forename: Guillermo
authors.initials: G
authors.lastname: Valdomir
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.
authors.forename: Soundararasu
authors.initials: S
authors.lastname: Senthilkumar
authors.affiliation: Institute of Organic and Biomolecular Chemistry, Georg-August University of Göttingen, Tammannstr. 2, 37077, Göttingen, Germany.
authors.forename: Lutz F
authors.initials: LF
authors.lastname: Tietze
mesh_terms: D002384:Catalysis; D003500:Cyclization; D019281:Dimerization; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014966:Xanthenes / Q000737:chemistry; D044004:Xanthones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D014966:Xanthenes; D044004:Xanthones; C436331:dicerandrol C; D010165:Palladium
keywords: Suzuki reaction; dicerandrols; enantioselectivity; heterocycles; natural products