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

Add time:07/19/2019    Source:sciencedirect.com

Ketalization of 7-oxo-dihydrothebainone (the antipode of sinomeninone) gave 6,6; 7,7-diethylenedioxy and 6,7; 6,7-diethylenedioxy derivatives depending on the amount of toluene-p-sulphonic acid. Ullmann reaction of these ketal derivatives and sodium-liquid ammonia reduction followed by hydrolysis gave 4-desoxy-7-oxo-dihydrothebainone. Hydrogen peroxide oxidation of the foregoing compound and cyclization of the dibasic acid gave (−)-3-methoxy-6-oxo-N-methyl-C-nor-morphinan.

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