title: Biomimetic synthesis of (±)-merochlorin B.
abstract: A short total synthesis, guided by biosynthetic considerations, of racemic merochlorin B is presented. The formation of its isomer, merochlorin A, was not observed under the conditions. Key steps include a directed ortho-metalation (DoM), a selective demethylation, an ortho-allylation, and an oxidative [3 + 2]-cycloaddition mediated by an iodine(III) reagent.
authors.affiliation: Department of Chemistry and Center for Integrated Protein Science, University of Munich (LMU) , Butenandtstraße 5-13, 81377 München, Germany.
authors.forename: Robin
authors.initials: R
authors.lastname: Meier
authors.forename: Sebastian
authors.initials: S
authors.lastname: Strych
authors.forename: Dirk
authors.initials: D
authors.lastname: Trauner
mesh_terms: D032701:Biomimetics; D061565:Cycloaddition Reaction; D007202:Indicators and Reagents; D007455:Iodine / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D054830:Sesterterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D007202:Indicators and Reagents; D054830:Sesterterpenes; C576411:merochlorin B; D007455:Iodine