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 asymm...

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Bibliographic Details
Published in:Journal of organic chemistry 1997-03, Vol.62 (6), p.1668-1674
Main Authors: Denmark, Scott E, Hurd, Alexander R, Sacha, Hubert J
Format: Article
Language:English
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Summary:(−)-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo962306n