title: Biomimetic asymmetric total syntheses of spirooliganones A and B.
abstract: Biomimetic total syntheses of potent antiviral spirooliganones A and B were achieved with 3% and 2% yield, respectively, in 12 steps from commercially available materials. The synthetic strategy was inspired primarily by the biogenetic hypothesis and was enabled by two independent cascade events: (i) an unprecedented reaction involving aromatic Claisen rearrangement/o-quinone methide formation/hetero-Diels-Alder cycloaddition to construct the tetracyclic framework and (ii) phenol oxidative dearomatization/spirocyclization to build the spiro-fused cyclohexadienone/tetrahydrofuran moiety.
authors: Department of Chemistry, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong, China.
authors: Liyan
authors: L
authors: Song
authors: Hongliang
authors: H
authors: Yao
authors: Rongbiao
authors: R
authors: Tong
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D032701:Biomimetics; D002522:Chlorocebus aethiops; D061565:Cycloaddition Reaction; D004285:Dogs; D045563:Indolequinones / Q000737:chemistry; D053122:Influenza A Virus, H3N2 Subtype / Q000187:drug effects*; D061985:Madin Darby Canine Kidney Cells / Q000187:drug effects; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D014709:Vero Cells / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D045563:Indolequinones; D013141:Spiro Compounds; C586354:spirooliganone A; C068040:quinone methide