title: Biomimetic total synthesis of malbrancheamide and malbrancheamide B.
abstract: The biomimetic total syntheses of both malbrancheamide and malbrancheamide B are reported. The synthesis of the two monochloro species enabled the structure of malbrancheamide B to be unambiguously assigned. The syntheses each feature an intramolecular Diels-Alder reaction of a 5-hydroxypyrazin-2(1H)-one to construct the bicyclo[2.2.2]diazaoctane core, which has also been proposed as the biosynthetic route to these compounds.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523-1872, USA.
authors.forename: Kenneth A
authors.initials: KA
authors.lastname: Miller
authors.forename: Timothy R
authors.initials: TR
authors.lastname: Welch
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Greshock
authors.forename: Yousong
authors.initials: Y
authors.lastname: Ding
authors.forename: David H
authors.initials: DH
authors.lastname: Sherman
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D000577:Amides / Q000737:chemistry; D032701:Biomimetics; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000577:Amides; D006576:Heterocyclic Compounds, 4 or More Rings; D026121:Indole Alkaloids; C529354:malbrancheamide