Tandem [4+2]/[3+2] cycloadditions of nitroalkenes. 9. Synthesis of (-)-rosmarinecine

Scott E. Denmark, Atli Thorarensen, Donald S. Middleton

Research output: Contribution to journalArticle

Abstract

(-)-Rosmarinecine (2) is the necine base portion of the pyrrolizidine alkaloid (-)-rosmarinine. (-)Rosmarinecine is a representative of the group of pyrrolizidines that show a cis relationship between adjacent stereocenters C(1), C(7), and C(7a), in addition to a highly oxygenated skeleton. (-)-Rosmarinecine (2) has been synthesized in eight steps and 14.8% overall yield, as an illustration of a general approach for the construction of pyrrolizidines having this stereochemical feature. The key step in the asymmetric synthesis is a Lewis acid-promoted, tandem inter-[4+2]/intra-[3+2] cycloaddition between a fumaroyloxy nitroalkene and a chiral vinyl ether.

Original languageEnglish (US)
Pages (from-to)8266-8277
Number of pages12
JournalJournal of the American Chemical Society
Volume118
Issue number35
DOIs
StatePublished - Sep 4 1996

ASJC Scopus subject areas

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

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