title: Our recent progress on the intramolecular Diels-Alder reaction approach in natural products synthesis: synthetic studies of the octahydronaphthalene substructure of versipelostatins and the A/B/C-tricyclic substructure of GKK1032s.
abstract: During this decade, the enantio- and stereoselective synthesis of natural products has been actively explored in the author's laboratory. In this account, the author outlines practical syntheses of the polycyclic substructures of two novel structurally formidable antibiotics, namely, the trans-fused octahydronaphthalene moiety of versipelostatins and the A/B/C-tricyclic decahydrofluorene moiety of GKK1032s. Both syntheses have been achieved with remarkable regio- and stereoselectivity via intramolecular Diels-Alder reactions using well-designed enantiomeric substrates.
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan. tadano@applc.keio.ac.jp.
authors.forename: Kin-Ichi
authors.initials: K
authors.lastname: Tadano
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction / Q000379:methods*; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D001688:Biological Products; D005449:Fluorenes; D006575:Heterocyclic Compounds, 3-Ring; D018942:Macrolides; D009844:Oligosaccharides; C490154:versipelostatin; C041509:fluorene
keywords: GKK1032s; antibiotics; intramolecular Diels-Alder reactions; total synthesis; versipelostatins