Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration.
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).
Ohtsuki
Keiko
K
Institute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasugako-en, Kasuga 816-8580, Japan.
Matsuo
Kazumasa
K
Yoshikawa
Takashi
T
Moriya
Chihiro
C
Tomita-Yokotani
Kaori
K
Shishido
Kozo
K
Shindo
Mitsuru
M
D000215:Acylation; D015394:Molecular Structure; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry
D014966:Xanthenes; C433844:sundiversifolide