Elimination of the 4-hydroxyl group of the alkaloids related to morphine—VIII

Add time:07/21/2019    Source:sciencedirect.com

The Ullmann reaction of β-tetrahydrodesoxycodeine and the successive sodium—liquid ammonia reduction gave (−)-3-methoxy-N-methylisomorphinan in excellent yield. Similar reduction of the ketal of β-dihydrothebainone phenyl ether followed by the hydrolysis gave the desired (−)-3-methoxy-6-oxo-N-methylisomorphinan, whereas a similar sequence of reactions with β-thebainone-A phenyl ether gave (−)-3-methoxy-6-oxo-N-methyl-Δ7-morphinan and the corresponding Δ7-isomorphinan derivative.

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