title: Efficient Synthetic Routes to (±)-Hippolachnin A, (±)-Gracilioethers E and F and the Alleged Structure of (±)-Gracilioether I.
abstract: Two monocyclic members in the gracilioether family were synthesized in only three steps. The monocyclic products were further elaborated into advanced precursors to hippolachnin A and gracilioether E, respectively. Gracilioether F and the alleged structure for gracilioether I were also synthesized using a late-stage C(sp3)-H thermo-oxidation.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Ze-Jun
authors.initials: ZJ
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.
authors.forename: Yikang
authors.identifier: http://orcid.org/0000-0003-4501-5401
authors.initials: Y
authors.lastname: Wu
mesh_terms: D061565:Cycloaddition Reaction; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D061065:Polyketides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D004988:Ethers, Cyclic; D006575:Heterocyclic Compounds, 3-Ring; D061065:Polyketides; C000607877:gracilioether E; C000600615:gracilioether F; C000626378:gracilioether I; C585986:hippolachnin A
keywords: condensation; cycloaddition; cyclocarbonylation; lactones; oxidation