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

(-)-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.