Synthetic Morphinans and Hasubanans. Part IV. Total Synthesis of 3,14-Dihydroxyisomorphinans, 3-Methoxy-Δ8,14-morphinans, and 9α-Hydroxy-3-methoxyhasubanan
- 1 September 1975
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 53 (17) , 2515-2523
- https://doi.org/10.1139/v75-358
Abstract
The synthesis of a versatile intermediate 4a-(2-aminoethyl)-l,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene (3a) and its utilization in the synthesis of 9α-hydroxy-3-methoxy-17-methylhasubanan (10), 3,14-dimethoxy-17-methylisomorphinan (9l), various 14-hydroxyisomorphinans (9), and 3-methoxy-Δ8,14-morphinan (11b) is described. A number of 17-alkyl-3,14-dihydroxyisomorphinans were prepared and tested for narcotic antagonist and analgesic activities in laboratory animals. Some of these new compounds have exhibited significant activities.Keywords
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