title: The first total synthesis of natural grenadamide.
abstract: A concise, high yielding route to the naturally occurring enantiomer of grenadamide utilizing a 3,6-disubstituted 1,2-dioxine starting material is presented. The route allows for ease in synthesizing grenadamide derivatives varying at cyclopropyl carbons 2 and 3, with access to both enantiomers. Evidence for phosphorus-assisted deprotonation of 1,2-dioxines is also discussed.
authors.affiliation: Department of Chemistry, University of Adelaide, South Australia 5005, Australia.
authors.forename: Thomas D
authors.initials: TD
authors.lastname: Avery
authors.forename: Julie A
authors.initials: JA
authors.lastname: Culbert
authors.forename: Dennis K
authors.initials: DK
authors.lastname: Taylor
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D003521:Cyclopropanes / Q000138:chemical synthesis*; D010758:Phosphorus; D013237:Stereoisomerism
chemical_list: D000577:Amides; D003521:Cyclopropanes; C112731:grenadamide; D010758:Phosphorus; C030797:cyclopropane