title: A robust synthesis of 7,8-didemethyl-8-hydroxy-5-deazariboflavin.
abstract: The biosynthetic precursor of redox cofactor F420, 7,8-didemethyl-8-hydroxy-5-deazariboflavin, was prepared in four steps from 6-chlorouracil, 2-chloro-4-hydroxybenzaldehyde and bis-isopropylidene protected D-ribose. The latter aldehyde was transformed to the corresponding protected ribitylamine via the oxime, which was submitted to reduction with LiAlH4. Key advantage compared to previous syntheses is the utilization of a polyol-protective group which allowed the chromatographic purification of a key-intermediate product providing the target compound with high purity.
authors.affiliation: Institut für Chemie, Universität Oldenburg, Carl von Ossietzky-Str. 9-11, D-26129 Oldenburg, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Bender
authors.affiliation: Institut für Biologie und Umweltwissenschaften, Universität Oldenburg, D-26111 Oldenburg, Germany; Centre for Neurosensory Sciences, University of Oldenburg, D-26111 Oldenburg, Germany.
authors.forename: Henrik
authors.initials: H
authors.lastname: Mouritsen
authors.affiliation: Institut für Chemie, Universität Oldenburg, Carl von Ossietzky-Str. 9-11, D-26129 Oldenburg, Germany.
authors.forename: Jens
authors.initials: J
authors.lastname: Christoffers
keywords: carbohydrates; heterocyclic compounds; protective groups; riboflavin derivatives; ribose derivatives