Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration |
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| Authors: | Ohtsuki Keiko Matsuo Kazumasa Yoshikawa Takashi Moriya Chihiro Tomita-Yokotani Kaori Shishido Kozo Shindo Mitsuru |
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| Affiliation: | Institute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasugako-en, Kasuga 816-8580, Japan. |
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| 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). |
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