title: Absolute configuration of anti-HIV-1 agent (-)-concentricolide: total synthesis of (+)-(R)-concentricolide.
abstract: The first enantioselective total synthesis of (+)-(R)-concentricolide, the enantiomer of an anti-HIV-1 agent isolated from Daldinia concentrica, from 2-iodophenol in 7 steps reveals the (S)-configuration for the natural form of the furanophthalide. The key features include an anionic ortho-Fries rearrangement to furnish 3-iodosalicylamide, facile construction of the benzofuran system employing the tandem Sonogashira coupling annulation reaction, directed ortho metalation to introduce a propanoyl group, as well as CBS reduction, establishing the stereocenter enantioselectively.
authors.affiliation: Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan 11529.
authors.forename: Chih-Wei
authors.initials: CW
authors.lastname: Chang
authors.forename: Rong-Jie
authors.initials: RJ
authors.lastname: Chein
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D019380:Anti-HIV Agents; D005663:Furans; D006575:Heterocyclic Compounds, 3-Ring; C560849:concentricolide