title: Stereoselective formation of tetrahydrofuran rings via [3 + 2] annulation: total synthesis of Plakortone L.
abstract: The [3 + 2] annulation of 2,3-O-isopropylidene-aldehydo-aldose with methallyl ether leads to the stereoselective formation of a substituted tetrahydrofuran system, which is converted to a bicyclic lactone derivative via consecutive deprotection, oxidative cleavage of the terminal diol, oxidation of the resulting lactol, and Barton-McCombie deoxygenation. The efficiency of this process was demonstrated by the first total synthesis of Plakortone L.
authors.affiliation: Department of Chemistry and Biological Science, Aoyama Gakuin University , 5-10-1, Fuchinobe, Chuo-ku, Sagamihara-shi 252-5258, Japan.
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Sugimura
authors.forename: Shougo
authors.initials: S
authors.lastname: Sato
authors.forename: Kensei
authors.initials: K
authors.lastname: Tokudome
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yamada
mesh_terms: D000818:Animals; D001315:Australia; D004986:Ether; D005663:Furans; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D005663:Furans; D007783:Lactones; C000590291:plakortone L; D004986:Ether; C018674:tetrahydrofuran