title: Oxidative coupling as a biomimetic approach to the synthesis of scytonemin.
abstract: The first total synthesis of the dimeric alkaloid pigment scytonemin is described. The key transformations in its synthesis from 3-indole acetic acid are a Heck carbocyclization and a Suzuki-Miyaura cross-coupling, orchestrated in a stereospecific tandem fashion, followed by a biosynthetically inspired oxidative dimerization. The tandem sequence generates a tetracyclic (E)-3-(arylidene)-3,4-dihydrocyclopenta[b]indol-2(1H)-one that is subsequently dimerized into the unique homodimeric core structure of scytonemin.
authors.affiliation: Department of Chemical and Biological Engineering/Organic Chemistry, Chalmers University of Technology, SE-412 96 Gothenburg, Sweden.
authors.forename: Andreas
authors.initials: A
authors.lastname: Ekebergh
authors.forename: Isabella
authors.initials: I
authors.lastname: Karlsson
authors.forename: Rudi
authors.initials: R
authors.lastname: Mete
authors.forename: Ye
authors.initials: Y
authors.lastname: Pan
authors.forename: Anna
authors.initials: A
authors.lastname: Börje
authors.forename: Jerker
authors.initials: J
authors.lastname: Mårtensson
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis*; D019281:Dimerization; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis*
chemical_list: D007211:Indoles; D010636:Phenols; C083368:scytonemin