Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration
Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration
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DOI：
10.1021/ol8001333
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发表时间：
2008-03-20
期刊：
影响因子：
5.2
通讯作者：
Shindo, Mitsuru
中科院分区：
文献类型：
--
作者：
Ohtsuki, Keiko;Matsuo, Kazumasa;Shindo, Mitsuru
有机锂的分子内酰化导致了一个有效的立体控制的全合成的两个对映体的sundiversifolide。通过高效液相色谱分析和化感作用测定确定了其绝对构型。由双环α-羟基半缩醛与Ph（3）P=CMe（CO（2）R）缩合得到γ-内酯部分。
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. They-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic alpha-hydroxyhemiacetal with Ph(3)P=CMe(CO(2)R).