title: Biomimetic total synthesis of gracilioethers B and C.
abstract: Total syntheses of the marine polyketide metabolites gracilioethers B and C have been realized in 9 steps (40% overall yield) and 10 steps (34% overall yield), respectively. The [2(5H)-furanylidene]ethanoate (furanylidene) motif was constructed in a transacetalization/dehydration cascade of an advanced β-ketoester intermediate, which was designed to mimic a postulated biosynthetic precursor to the natural products. The relative and absolute configurations of gracilioethers B and C are confirmed as (6R,8R) and (6R,8R,11S), respectively.
authors.affiliation: School of Chemical and Physical Sciences, Flinders University , GPO Box 2100, Adelaide, SA 5001, Australia.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Norris
authors.forename: Michael V
authors.initials: MV
authors.lastname: Perkins
authors.forename: Erik J
authors.initials: EJ
authors.lastname: Sorensen
mesh_terms: D001688:Biological Products; D032701:Biomimetics; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D005663:Furans; C542748:gracilioether B; C542749:gracilioether C