Copper(I) iodide-promoted hydroxylation onto the lithium or potassium enolate of lactones and lactams

After enolization of lactones (1a,b) and lactams (2a,b) with lithium or pot assium hexamethyidisilazide in THF, each resultant enolate was treated with a solution prepared by mixing copper(I) iodide, pyridine, and tert-butyl h ydroperoxide or N-methylmorpholine N-oxide in THF to give a-hydroxy lactone s (3a,b) and a-hydroxy lactams (4a,b) in satisfied yields. This hydroxylati on method was successfully applied to conversion of dI-desoxycamptothecin ( dI-7) to dl-camptothecin (dI-5).