Abstract
The synthesis of 7, 8-dihydroxy-1, 2, 3, 4, 5, 6-hexahydro-2, 6-methano-3-benzazocin-1-ol (6) was undertaken in an attempt 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 (1) might be essential for the β-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, by way of 14, 15, and 16. Compound 6 was derived from 17 by a five-step sequence of reactions. The β-adrenoceptor activity of 6, in which the amino moiety is fixed in an axial conformation, proved to be about one-thousandth of that of l-isoproterenol.
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