The synthesis of 7,8-dihydroxy-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-1-ol.

Publisher Website
Google Scholar
Abstract
The synthesis of 7,8-dihydroxy-1,2,3,4,5,6,-hexahydro-2,6-methano-3-benzaozocin-1-ol (6) was undertaken to confirm the hypothesis that an equatorial conformation of the amino group in 2-amino-5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthalenol derivatives might be essential for the .beta.-adrenoceptor activity. 4-(2,3-Dimethoxyphenyl)cyclohexanone (13) which was prepared via several steps from 2,3-dimethoxyphenylacetonitrile (7), was led to a tetralone derivatives (17) by oxime formation, Beckmann rearrangement, hydrolysis and cyclization. Compound 6 was derived from 17 by a 5 step sequence of reactions. The .beta.-adrenoceptor activity of 6, in which the amino moiety is fixed in an axial conformation, proved to be .apprx. 1/1000 of that of l-isoproterenol in isolated guinea pig tracheal strips.

This publication has 1 reference indexed in Scilit: