187840-87-5Relevant academic research and scientific papers
Tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes. 13. The synthesis of (-)-detoxinine
Denmark, Scott E.,Hurd, Alexander R.,Sacha, Hubert J.
, p. 1668 - 1674 (2007/10/03)
(-)-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.
