(-)-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.
(-)-脱色素杆菌素是一种独特的多官能团
氨基酸,它是 detoxin 复合物诸多组分的核心残基。其合成过程通过十步反应,以二
氯二异丙基硅烷作为起始原料,最终获得了13.4%的总体产率。反应的关键步骤是利用
硅氧基的
乙烯基醚对硝基烯烃进行串联合环反应,即'4+2'加成反应和'3+2'加成反应,这一过程展现出
硅基连接物在硝基烯烃串联合成中的巧妙应用。其合成路径的核心在于对硝基烯烃进行逻辑型协同合成。