title: The synthesis of melohenine B and a related natural product.
abstract: A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.
authors.affiliation: School of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews, Fife KY16 9ST, UK.
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Lancefield
authors.forename: Linna
authors.initials: L
authors.lastname: Zhou
authors.forename: Tomas
authors.initials: T
authors.lastname: Lébl
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Westwood
mesh_terms: D029062:Apocynaceae / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D046948:Secologanin Tryptamine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014748:Vinca Alkaloids / Q000737:chemistry*
chemical_list: D001688:Biological Products; D046948:Secologanin Tryptamine Alkaloids; D014748:Vinca Alkaloids; C545603:melohenine B; C016422:eburnamonine