title: Total synthesis of sphingofungin E from D-glucose.
abstract: [reaction: see text] Total synthesis of sphingofungin E (1) is described. Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose generated tetra-substituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized part in sphingofungin E (4) stereoselectively. Coupling reaction of 4 with the C(12) hydrophobic part, followed by further manipulation, completed the total synthesis.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522 Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Oishi
authors.forename: Koji
authors.initials: K
authors.lastname: Ando
authors.forename: Kenjin
authors.initials: K
authors.lastname: Inomiya
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Sato
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Iida
authors.forename: Noritaka
authors.initials: N
authors.lastname: Chida
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry*; D007202:Indicators and Reagents; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000935:Antifungal Agents; D005231:Fatty Acids, Unsaturated; D007202:Indicators and Reagents; C078943:sphingofungin E; D005947:Glucose