PlumX Metrics
Embed PlumX Metrics

Stereoselective synthesis of 3-oxygenated-ds-dialkyl-2,5-substituted tetrahydrofurans from cyclohexadienediols

Journal of Organic Chemistry, ISSN: 0022-3263, Vol: 73, Issue: 15, Page: 5776-5785
2008
  • 16
    Citations
  • 0
    Usage
  • 11
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

Article Description

(Chemical Equation Presented) The 3-oxygenated-cis-dialkyl-2,5-substituted tetrahydrofuran system, present in several natural products, was prepared with good selectivity by acidic cyclization of 5-alkene-1,2,4-triol derivatives. The starting alkenol was obtained in few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The study of the cyclization allowed the rationalization of all experimental results by assuming a complete ionization at the allylic position and a model close to the one proposed by Labelle for homoallylic induction in five-membered ring closures. © 2008 American Chemical Society.

Bibliographic Details

Provide Feedback

Have ideas for a new metric? Would you like to see something else here?Let us know