title: Xylochemistry--Making Natural Products Entirely from Wood.
abstract: The first total synthesis of the dimeric berberine alkaloid ilicifoline (ilicifoline B) is reported. Its carbon skeleton is constructed from ferulic acid, veratrole, and methanol. The synthesis reported herein employs starting materials solely derived from wood. The natural product is thus constructed entirely from renewable resources. The same strategy is applied to a formal total synthesis of morphinan alkaloids. The use of wood-derived building blocks (xylochemicals) instead of the conventional petrochemicals represents a sustainable alternative to classical synthetic approaches.
authors.affiliation: Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10-14, 55128 Mainz (Germany).
authors.forename: Daniel
authors.initials: D
authors.lastname: Stubba
authors.affiliation: Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10-14, 55128 Mainz (Germany).
authors.forename: Günther
authors.initials: G
authors.lastname: Lahm
authors.affiliation: Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10-14, 55128 Mainz (Germany).
authors.forename: Mario
authors.initials: M
authors.lastname: Geffe
authors.affiliation: The University of Alabama, Department of Chemistry (USA).
authors.forename: Jason W
authors.initials: JW
authors.lastname: Runyon
authors.affiliation: The University of Alabama, Department of Chemistry (USA). aj@ajarduengo.net.
authors.forename: Anthony J
authors.initials: AJ
authors.lastname: Arduengo
authors.affiliation: Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10-14, 55128 Mainz (Germany). opatz@uni-mainz.de.
authors.forename: Till
authors.initials: T
authors.lastname: Opatz
mesh_terms: D001600:Berberine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D014934:Wood / Q000737:chemistry*
chemical_list: D001600:Berberine Alkaloids; D001688:Biological Products; C000610328:ilicifoline B
keywords: alkaloids; nitrogen heterocycles; sustainable chemistry; total synthesis; xylochemistry