Practical and High-Yield Syntheses of Dihydromorphine from Tetrahydrothebaine and Efficient Syntheses of (8<i>S</i>)-8-Bromomorphide
作者:Anna K. Przybyl、Judith L. Flippen-Anderson、Arthur E. Jacobson、Kenner C. Rice
DOI:10.1021/jo0206871
日期:2003.3.1
A practical method for the conversion of tetrahydrothebaine to dihydromorphine in 92% yield is described. The procedure should allow more efficient production of opium products and may be easily modified for large-scale synthesis. The conversion of codeine to (8S)-8-bromomorphide, a potentially valuable intermediate to 6-demethoxyoripavine and derivatives, is also described. The absolute configuration of (8S)-8-bromomorphide was determined by a single-crystal X-ray diffraction study of the hydrobromide salt.