Novel approach toward the morphine skeleton. Synthesis of 1-(5-benzyloxy-2-bromo-4-methoxybenzyl)-6-oxo-3,4,6,7,8,8a-hexahydro-1H-isoquinoline-2-carboxylic acid phenyl ester via N-acylpyridinium salt chemistry

A dihydropyridone-mediated approach to the morphine skeleton was investigated. The hexahydroisoquinoline 2 was synthesized in nine steps using N-acylpyridinium chemistry and dihydropyridone functionalization methods. This new approach should be useful in the design of more efficient syntheses of morphine and its derivatives.

Figure optionsDownload high-quality image (97 K)Download as PowerPoint slide