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

SE Denmark, AR Hurd, HJ Sacha

Index: Denmark, Scott E.; Hurd, Alexander R.; Sacha, Hubert J. Journal of Organic Chemistry, 1997 , vol. 62, # 6 p. 1668 - 1674

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Citation Number: 90

Abstract

(-)-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 ...