title: Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach.
abstract: [reaction: see text]. Starting from diethyl (R)-malate, synthesis of the lower-half segment of (+)-tubelactomicin A, a 16-membered macrolide antibiotic, has been achieved. The synthesis involved the highly endo- and pi-facial selective intramolecular Diels-Alder reaction achieved using a trisubstituted methacrolein derivative tethering a 10-carbon dienyne unit at the beta-carbon, which in turn was prepared from a known allylated malic acid derivative.
authors.affiliation: Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Toru
authors.initials: T
authors.lastname: Motozaki
authors.forename: Kiyoto
authors.initials: K
authors.lastname: Sawamura
authors.forename: Akari
authors.initials: A
authors.lastname: Suzuki
authors.forename: Keigo
authors.initials: K
authors.lastname: Yoshida
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Ueki
authors.forename: Aiko
authors.initials: A
authors.lastname: Ohara
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: D000190:Actinomyces / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008293:Malates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D007783:Lactones; D018942:Macrolides; D008293:Malates; C418197:tubelactomicin A