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

页码：1668 / 1674

页数：7

共 71 条

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