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

Scott E. Denmark, Alexander R. Hurd, Hubert J. Sacha

Research output: Contribution to journalArticle

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 application of a temporary silicon tether in the tandem nitroalkene cycloaddition process.

Original languageEnglish (US)
Pages (from-to)1668-1674
Number of pages7
JournalJournal of Organic Chemistry
Volume62
Issue number6
DOIs
StatePublished - Jan 1 1997

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this