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Communication | Regular issue | Vol 6, No. 8, 1977, pp.1157-1165
Published online, 1st January, 1970
DOI: 10.3987/R-1977-08-1157
■ Studies in the (+)-Morphinan Series I. An Alternative Conversion of (+)-Dihydrocodeinone into (+)-Codeine

Ikuo Iijima, Kenner C. Rice,* and J. V. Silverton

*Metabolism, Laboratory of Chemistry, National Institute of Arthritis, Bethesda, Maryland 20014, U.S.A.

Abstract

A novel four-step transformation of (+)-dihydrocodeinone (1) to unnatural (+)-codeine (5) via N-carbethoxy-7-phenylselenonordihydrocodeinone (3) (40% overall yield) is described. The structure and absolute configuration of 3 were confirmed by single crystal X-ray analysis.