Intramolecular [6 + 4] and [4 4+ 2] Tropone-Olefin Cycloaddition Reactions. Facile Synthesis of the Ingenane Ring System

Raymond Lee Funk, Gary L. Bolton

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Abstract

The intermolecular [6 + 4] and [4 + 2] cycloaddition reactions of tropone with dienes and monoenes, respectively, have been extensively examined and exploited in recent synthetic endeavors. Surprisingly, there has not been an investigation of the intra- c All new compounds reported herein exhibited satisfactory spectral (IR, NMR), analytical, and/or high-resolution mass spectral characteristics. Contaminated by ~10% tropone 17 (13C NMR analysis). Yield based on recovered starting material (4%) and product contaminated with 18 (6%, 1H NMR analysis). Yield based on recovered starting materials (10%) and product contaminated with 18 (3%, 1H NMR analysis). Yield based on recovered 21 (42%).

Original languageEnglish (US)
Pages (from-to)4655-4657
Number of pages3
JournalJournal of the American Chemical Society
Volume108
Issue number15
DOIs
Publication statusPublished - Jan 1 1986

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All Science Journal Classification (ASJC) codes

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

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