Aqueous Dearomatization/Diels–Alder Cascade to a Grandifloracin Precursor

• Emily A. Shimizu ^[1] ; Brett Cory ^[2] ; Johnson Hoang ^[1] ; Giovanni G. Castro ^[1] ; Michael E. Jung ^[2] ; David A. Vosburg ^[1]
  1. [1] Harvey Mudd College

     Harvey Mudd College

     Estados Unidos

     
  2. [2] University of California, United States
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 96, Nº 5, 2019, págs. 998-1001
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • A green laboratory experiment has been developed in which students perform an aqueous oxidation/cycloaddition reaction to convert salicyl alcohol into a pentacyclic diepoxydione that is readily isolated by filtration. Drawing on their knowledge of periodate-mediated 1,2-diol cleavage, students propose a mechanism for the oxidation of salicyl alcohol (which is not a 1,2-diol) and the structure of the transient product (prior to a spontaneous Diels–Alder dimerization). Students then characterize salicyl alcohol and their diepoxide product by mass spectrometry, IR spectroscopy, and 1H, 13C, and two-dimensional NMR spectroscopy. The only organic solvents used are small amounts for IR and NMR spectroscopy.