Copper(I) Iodide-Promoted Hydroxylation onto The Lithium or Potassium Enolate of Lactones and Lactams

摘要

After eolization of lactones (1a,b) and lactams (2a,b) with lithium or potassium hexamethyldisilazide in THF, each resultant enolate was treated with a solution prepared by mixing copper(I) iodide, pyridine, and tert-butyl hydropeorxide or N-methylmorpholine N-oxide in THF to give #alpha#-hydroxy lactones (3a, b) and #alpha#-hydroxy lactams (4a,b) in satisfied yields. This hydroxylation method was successfully applied to conversion of dl-desoxycamptothecin (dl-7) to dl-camptothecin (dl-5).