Bis Heteroannulation. 2. Oxazole Alcohols from the Interaction of Lithiomethyl Isocyanide with Lactones. A Novel Synthesis of Evodone

Article abstract of DOI:10.1021/jo00323a017

Oxazole alcohols may be readily obtained through the interaction of lithiomethyl isocyanide with lactones.Acetylenic oxazoles of proper design have been shown to undergo a facile intramolecular Diels-Alder reaction, leading directly to fused-ring furan derivatives of the type found in the furanosesquiterpenes ("bis heteroannulation").A novel synthesis of evodone is presented.