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Paper | Regular issue | Vol 55, No. 11, 2001, pp.2157-2170
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9330
■ Copper(I) Iodide-promoted Hydroxylation onto the Lithium or Potassium Enolate of Lactones and Lactams

Norio Nakazawa, Keiko Tagami, Hitoshi Iimori, Shigeki Sano, Tsutomu Ishikawa, and Yoshimitsu Nagao*

*Sho-machi, Tokushima 770-8505, Japan

Abstract

After enolization 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 hydroperoxide or N-methylmorpholine N-oxide in THF to give α-hydroxy lactones (3a,b) and α-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).