Journal of medicinal chemistry

Synthesis of thebaine and oripavine from codeine and morphine

RB Barber, H Rapoport

Index: Barber,R.B.; Rapoport,H. Journal of Medicinal Chemistry, 1975 , vol. 18, p. 1074 - 1077

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Citation Number: 42

Abstract

A practical synthesis of thebaine and oripavine has been developed from codeine and morphine, respectively. Attempts to use a codeinone intermediate gave poor yields; however, methylation of the potassium salt of codeine to give codeine methyl ether followed by oxidation with y-MnOz gave thebaine in 67% yield from codeine. Similarly, the potassium salt of the di-0-anion of morphine was selectively alkylated to give morphine 6-methyl ...