A. Brossi, J. V. Burik, S. Teitel
Oct 31, 1968
Citations
0
Influential Citations
19
Citations
Journal
Helvetica Chimica Acta
Abstract
Polymethoxylated 1-phenethyl-3, 4-dihydro- and -1, 2, 3, 4-tetrahydro-isoquinolines were selectively demethylated by varying the mineral acid treatment. Under these conditions, the 6-methoxyl was the most stable, while the 4′-methoxyl was the most labile. Based on this study and by employing an unprotected phenolic intermediate in the Bischler-Napieralski cyclization, an efficient, simple and technically feasible synthesis of the diphenol 1, an important intermediate in the synthesis of homoapomorphine alkaloids, was achieved.