Tandem [4+2]/[3+2] cycloadditions of nitroalkenes .13. The synthesis of (-)-detoxinine

被引：86
|
作者：
Denmark, SE
Hurd, AR
Sacha, HJ
机构：
[1] Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 06期
关键词：
D O I：
10.1021/jo962306n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(-)-Detoxinine, an unusual, highly-functionalized amino acid, is the core residue of many components that comprise the detoxin complex. The synthesis of(-)-detoxinine was accomplished in 10 steps and 13.4% overall yield from commercially available dichlorodiisopropylsilane. The key step is an asymmetric tandem inter [4 + 2]/intra [3 + 2] cycloaddition between silyoxynitroalkene 17 and chiral vinyl ether (-)-24, illustrating the application of a temporary silicon tether in the tandem nitroalkene cycloaddition process.
引用
收藏
页码：1668 / 1674
页数：7
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