Enantioselective total synthesis of cyathin A3

被引：41
|
作者：
Ward, Dale E. [1 ]
Shen, Jianheng [1 ]
机构：
[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 15期
关键词：
D O I：
10.1021/ol070994z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of (-)-cyathin A(3) is described. The key step involves an unusual enantioselective Diels-Alder reaction of 2,5-dimethyl-1,4-benzoquinone with 2,4-bis(trimethylsilyloxy)-1,3-pentadiene, using Mikami's catalyst [(R)-BINOL + Cl2Ti((OPr)-Pr-i)(2) + 4 A mol sieves] modified by addition of Mg and SiO2. Because cyathin A(3) is easily transformed into allocyathin B-3, cyathin B-3, cyathin C-3, and neoallocyathin A(4), this route also constitutes formal syntheses of these natural products.
引用
收藏
页码：2843 / 2846
页数：4
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