Development of the 1,2-oxaza-Cope rearrangement.
A method for a concise assembly of oxazine rings based on a Lewis acid-promoted hetero-Cope rearrangement is described. The hetero-Cope rearrangement features the first examples of the [3,3]-sigmatropic transpositions involving the nitroso group. A variety of functionalized substrates have been subjected to the reaction. The described method has a strong potential for the synthesis of marine natural products containing oxazine rings.
Zakarian
Armen
A
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. zakarian@chem.fsu.edu
Lu
Chong-Dao
CD
D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry*
D010078:Oxazines