title: Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration.
abstract: Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The gamma-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic alpha-hydroxyhemiacetal with Ph3P=CMe(CO2R).
authors.affiliation: Institute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasugako-en, Kasuga 816-8580, Japan.
authors.forename: Keiko
authors.initials: K
authors.lastname: Ohtsuki
authors.forename: Kazumasa
authors.initials: K
authors.lastname: Matsuo
authors.forename: Takashi
authors.initials: T
authors.lastname: Yoshikawa
authors.forename: Chihiro
authors.initials: C
authors.lastname: Moriya
authors.forename: Kaori
authors.initials: K
authors.lastname: Tomita-Yokotani
authors.forename: Kozo
authors.initials: K
authors.lastname: Shishido
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Shindo
mesh_terms: D000215:Acylation; D015394:Molecular Structure; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D014966:Xanthenes; C433844:sundiversifolide