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

页码：2843 / 2846

页数：4

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