title: Total synthesis of gracilioether F: development and application of lewis Acid promoted ketene-alkene [2+2] cycloadditions and late-stage C-H oxidation.
abstract: The first synthesis of gracilioether F, a polyketide natural product with an unusual tricyclic core and five contiguous stereocenters, is described. Key steps of the synthesis include a Lewis acid promoted ketene-alkene [2+2] cycloaddition and a late-stage carboxylic acid directed C(sp(3) )H oxidation. The synthesis requires only eight steps from norbornadiene.
authors.affiliation: Department of Chemistry, Indiana University, 800 E. Kirkwood Ave, Bloomington, IN 47401 (USA).
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Rasik
authors.forename: M Kevin
authors.initials: MK
authors.lastname: Brown
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D061565:Cycloaddition Reaction; D005030:Ethylenes / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000475:Alkenes; D005030:Ethylenes; D006575:Heterocyclic Compounds, 3-Ring; D007659:Ketones; D058116:Lewis Acids; C000600615:gracilioether F; D002244:Carbon; D006859:Hydrogen; C008223:ketene
keywords: CH oxidation; cycloaddition; gracilioether F; ketenes; total synthesis