Tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes. 11. The synthesis of (+)-crotanecine

Scott E. Denmark, Atli Thorarensen

Research output: Contribution to journalArticle

Abstract

(+)-Crotanecine (1) is the necine base component of a number of pyrrolizidine alkaloids. This necine subunit is an amino triol bearing a primary allylic alcohol characterized by an all-cis relationship of its stereocenters. The synthesis of (+)-crotanecine has been accomplished in 10 steps and 10.2% overall yield. The key step in the asymmetric synthesis is a Lewis acid-promoted, tandem inter[4 + 2]/intra[3 + 2] cycloaddition between a (fumaroyloxy)nitroalkene 14 and chiral β-silylvinyl ether (-)-26. This synthesis serves to illustrate the synthetic versatility of the tandem cycloaddition to incorporate additional functionality.

Original languageEnglish (US)
Pages (from-to)125-137
Number of pages13
JournalJournal of the American Chemical Society
Volume119
Issue number1
DOIs
StatePublished - Jan 8 1997

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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