3-N,N-Dimethylamino-3-deoxy lincomycin: A structure-based hybrid between lincomycin and the desosamine unit of erythromycin

The observation that the desosamine sugar unit in erythromycin and the methyl thiolincosaminide portion of lincomycin occupy virtually identical sites on the 23S rRNA according to X-ray crystallograpaic data, instigated the synthesis of 3-N,N-dimethylamino-3-deoxy lincomycin as a hybrid structure. The synthesis in eight steps from lincomycin, involving a trans-diequatorial opening of an intermediate epoxide as the key step, is described.

The synthesis of 3-N,N-dimethylamino-3-deoxylincomycin is described.Figure optionsDownload as PowerPoint slide