title: Total syntheses of natural tubelactomicins B, D, and E: establishment of their stereochemistries.
abstract: Total syntheses of the antimicrobial tricyclic 16-membered macrolides, (+)-tubelactomicin B, (+)-tubelactomicin D, and (+)-tubelactomicin E, have been accomplished for the first time with common synthetic approaches. These total syntheses established the relative and absolute configurations of the three tubelactomicins, for which planar structures had solely been reported. The total synthesis of (+)-tubelactomicin D included a newly developed stereoselective intramolecular Diels-Alder reaction for constructing the highly functionalized octahydronaphthalene substructures.
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Kiyoto
authors.initials: K
authors.lastname: Sawamura
authors.forename: Keigo
authors.initials: K
authors.lastname: Yoshida
authors.forename: Akari
authors.initials: A
authors.lastname: Suzuki
authors.forename: Toru
authors.initials: T
authors.lastname: Motozaki
authors.forename: Ikuko
authors.initials: I
authors.lastname: Kozawa
authors.forename: Takashi
authors.initials: T
authors.lastname: Hayamizu
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Munakata
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Takao
authors.forename: Kin-ichi
authors.initials: K
authors.lastname: Tadano
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D018942:Macrolides; D009281:Naphthalenes; C523078:tubelactomicin B; C523081:tubelactomicin D; C523082:tubelactomicin E; C031721:naphthalene